{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-454464b52369433a8964eca6dbfa5e8b","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"fc928bb8eb5be2761e91b2645b56a603f7d48a2941445820917cf3f1128e250a","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-454464b52369433a8964eca6dbfa5e8b-a501f8ee8a9b","ord-454464b52369433a8964eca6dbfa5e8b-eec162cc4f83"],"reactant_slugs":["ord-compound-2cdc7a0a95679fad702d","ord-compound-c548c24d29328ab9f616"],"product_slugs":["ord-compound-6e4dea09de97fbb78f89"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lsf_lit_minisci_111"},{"type":"CUSTOM","details":"rxn_tech from SURF table","value":"alkylation"},{"type":"REACTION_TYPE","details":"alkylation minisci","value":"alkylation minisci"}],"inputs":{"additive_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)(O)O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7664-93-9"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)N1CC(I)C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"254454-54-1"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1N=C(OC)C=CC1OC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"4603-59-2"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Fe].O=S(=O)(O)O.O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7782-63-0"}],"amount":{"moles":{"value":0.3,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OO"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7722-84-1"}],"amount":{"moles":{"value":3,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7732-18-5"}],"amount":{"volume":{"value":0.3,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"67-68-5"}],"amount":{"volume":{"value":4.7,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"notes":{"procedure_details":"H2O2 (30% in H2O; 0.15 mL, 1.5 mmol) was added over 1 min to a stirred solution of 3,6-dimethoxypyridazine 1e (67 mg, 0.5 mmol), concentrated  H2SO4  (51  μL,  1.0  mmol),  1-Boc-3-(iodo)azetidine  (271  mg,  1.0  mmol)  and  iron(II)   - 14 -sulfate heptahydrate (40 mg, 0.15 mmol) in DMSO (5 mL) at room temperature. The mixture was then placed in an oil bath at 60 °C. After 2 min a further portion of iron(II) sulfate heptahydrate (40 mg, 0.15 mmol) was added and the mixture was stirred at 60 °C for 30 min. Further H2O2 (0.15 mL, 1.5 mmol) and  iron(II)  sulfate  heptahydrate  (40 mg, 0.15 mmol) was added, and the mixture was stirred at 60 °C for another 30 min. A final aliquot of  H2O2 (0.15 mL, 1.5 mmol) and iron(II) sulfate heptahydrate (40 mg, 0.15 mmol) was added and the mixture was stirred at 60 °C for another 30 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (15 mL) and Et2O (25 mL). The aqueous and  organic  layers  were  partitioned  and  the  aqueous  was  extracted  with  Et2O  (2  x  15  mL).  The  combined  organic  layers  were  washed  with  brine  (25  mL),  dried  (MgSO4),  filtered  and  the  solvent  removed under vacuum to leave a crude oil (408 mg). The oil was purified by column chromatography on silica gel using EtOAc / hexanes (0:1 to 1:1) as eluent to give the desired product 3d (57 mg, 41%) as an oil"},"outcomes":[{"reaction_time":{"value":1,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)N1CC(C2=CC(=NN=C2OC)OC)C1"},{"type":"CAS_NUMBER","value":"1180653-87-5"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":41}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz; CDCl3) δ 6.85 (d, J = 0.9 Hz, 1H), 4.27 (t, J = 8.7 Hz, 2H), 4.06 (s, 6H), 3.96 (t, J = 7.5 Hz, 2H), 3.83-3.76 (m, 1H), 1.45 (s, 9H); 13C NMR (100 MHz; CDCl3) δ 162.5, 160.5, 156.4, 135.1, 117.5, 80.0, 54.9, 53.4, 28.5, 28.2"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"MS of product_1":{"type":"MS","details":"296.16","data":{"found":{"float_value":296.16,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-2cdc7a0a95679fad702d","name":"C6H8N2O2 · ORD HKQOBAGKDBSVEQ-UHFFFAOYSA-N","smiles":"COc1ccc(OC)nn1","inchi":"InChI=1S/C6H8N2O2/c1-9-5-3-4-6(10-2)8-7-5/h3-4H,1-2H3","formula":"C6H8N2O2"},{"slug":"ord-compound-c548c24d29328ab9f616","name":"C8H14INO2 · ORD XPDIKRMPZNLBAC-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)N1CC(I)C1","inchi":"InChI=1S/C8H14INO2/c1-8(2,3)12-7(11)10-4-6(9)5-10/h6H,4-5H2,1-3H3","formula":"C8H14INO2"},{"slug":"ord-compound-6e4dea09de97fbb78f89","name":"C14H21N3O4 · ORD MHXAKZBKGCDOCO-UHFFFAOYSA-N","smiles":"COc1cc(C2CN(C(=O)OC(C)(C)C)C2)c(OC)nn1","inchi":"InChI=1S/C14H21N3O4/c1-14(2,3)21-13(18)17-7-9(8-17)10-6-11(19-4)15-16-12(10)20-5/h6,9H,7-8H2,1-5H3","formula":"C14H21N3O4"}],"dataset":{"dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","name":"Minisci dataset from Roche","description":"Minisci reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":130,"path":"data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","sha256":"ebefbe9aba687f182d4f068e94be0f7fd71d1189bdb2eff2aca6fedf4d522bf3","bytes":37643,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet"},"publication":{"slug":"ord-publication-91c8bf15879e5ce2","title":"Literature experiment — 10.1021/jo9010624","source_type":"paper","doi":"10.1021/jo9010624","url":"https://doi.org/10.1021/jo9010624","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}