Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-(Benzenesulfonyl)-3-phenyloxaziridine | HCID 320405 | — |
| Reactant | 5-Pyrimidinecarboxamide, 2-[(1-methylcyclopropyl)amino]-4-(methylthio)- | HCID 71237106 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | HCID 71237203 | HCID 71237203 | 74.4% |
Reaction Steps
To a stirring solution of 2-(1-methylcyclopropylamino)-4-(methylthio)-pyrimidine-5-carboxamide (305 mg, 1.280 mmol) in chloroform (25.6 mL) was added portionwise 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (502 mg, 1.920 mmol). The resulting pale yellow solution was stirred at ambient temperature overnight. The reaction solution was concentrated under reduced pressure to give crude product as a white solid. Ethyl acetate (10 mL) was added and the slurry was stirred at room temperature for 1 h, filtered, washed with ethyl acetate, and dried in a vacuum oven for a few hours to afford 2-(1-methylcyclopropylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamide (242 mg, 0.952 mmol, 74.4% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.35-8.90 (m, 2H), 7.88-8.14 (m, 1H), 7.28-7.59 (m, 1H), 2.74 (s, 3H), 1.32-1.46 (m, 3H), 0.68-0.84 (m, 2H), 0.50-0.70 (m, 2H). MS (ESI) m/z 255.0 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09139534B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-bb93b3dfae9f4d52b739cc99213824a8 |
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| Source note | uspto-grants-2015_09 |
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