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

HRID 2280799ノート

反応式

HRID 2280799 の反応式
[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

参加物

7

反応物 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 71237560HCID 71237560、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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]+.

後処理

  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.

出典と根拠

ORDレコード
ord-80d5b2de66ba4616b88a7bc9ba697bff
出典データセット
uspto-grants-2015_09
特許番号
US09139534B2

反応ノート

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