Hydrogen Peroxide → 5-Pyrimidinecarboxamide, 2-[(1-methylcyclopropyl)amino]-4-(methylthio)-
Reaction equation
[CH3:1][C:2]1([NH:5][C:6]2[N:11]=[C:10]([S:12][CH3:13])[C:9]([C:14]#[N:15])=[CH:8][N:7]=2)[CH2:4][CH2:3]1.[OH-:16].[Na+].OO>CS(C)=O.C(OCC)(=O)C.O>[CH3:1][C:2]1([NH:5][C:6]2[N:11]=[C:10]([S:12][CH3:13])[C:9]([C:14]([NH2:15])=[O:16])=[CH:8][N:7]=2)[CH2:4][CH2:3]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
To a stirring solution of 2-(1-methylcyclopropylamino)-4-(methylthio)pyrimidine-5-carbonitrile (0.653 g, 2.96 mmol, synthesis described herein) in DMSO (8 mL) was added 6N aqueous sodium hydroxide (2.470 mL, 14.82 mmol) solution and 30% aqueous hydrogen peroxide solution (1.873 mL, 16.52 mmol) at 0° C. Then the mixture was stirred at 50° C. and for 20 minutes and was then diluted with 100 mL ethyl acetate and 30 mL water. The layers were separated and the aqueous layer was back extracted with 50 mL ethyl acetate. The combined ethyl acetate layers were dried over anhydrous magnesium sulfate, filtered and concentrated to solids that were dried in a vacuum oven at 45° C. to afford 2-(1-methylcyclopropylamino)-4-(methylthio)pyrimidine-5-carboxamide (305 mg, 1.280 mmol, 43.2% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.31-8.54 (m, 1H), 7.80-8.07 (m, 1H), 6.97-7.77 (m, 1H), 2.39 (br. s., 3H), 1.37 (s, 3H), 0.52-0.79 (m, 4H). MS (ESI) m/z 239.0 [M+1]+.
Workup
- customThe layers were separated
- extractionthe aqueous layer was back extracted with 50 mL ethyl acetate
- dry with materialThe combined ethyl acetate layers were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to solids that
- customwere dried in a vacuum oven at 45° C.
Sources & evidence
- ORD record
- ord-80d5b2de66ba4616b88a7bc9ba697bff
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139534B2
Reaction notes
Loading…