Hydrogen Peroxide → 5-Pyrimidinecarboxamide, 2-[(1-methylcyclopropyl)amino]-4-(methylthio)-

HRID 2280799노트

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HRID 2280799 반응식
[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]1

참가 물질

7

반응물 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 71237560HCID 71237560, 화합물

생성물 1

HCID 712371065-Pyrimidinecarboxamide, 2-[(1-methylcyclopropyl)amino]-4-(methylthio)-수율 43.2%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

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]+.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was back extracted with 50 mL ethyl acetate
  3. dry with materialThe combined ethyl acetate layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to solids that
  6. customwere dried in a vacuum oven at 45° C.

출처 및 근거

ORD 기록
ord-80d5b2de66ba4616b88a7bc9ba697bff
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139534B2

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