Ethanol → 5-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine

HRID 220084

반응식

HRID 220084 반응식
[CH3:1][S:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][NH2:10])[CH:4]=1.N=[C:12]([CH3:16])[CH2:13][C:14]#[N:15].C(O)C>C(OCC)(=O)C>[CH3:16][C:12]1[CH:13]=[C:14]([NH2:15])[N:9]([C:5]2[CH:4]=[C:3]([S:2][CH3:1])[N:8]=[CH:7][N:6]=2)[N:10]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 70698Butanenitrile, 3-imino-HCID 135198554-Hydrazinyl-6-(methylthio)pyrimidine

생성물 1

HCID 591733685-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

The mixture of (6-Methylsulfanyl-pyrimidin-4-yl)-hydrazine (1.0 g, 6.4 mmol), 3-Imino-butyronitrile (1.1 g, 12.8 mmol), and ethanol (30 mL) is heated to 85° C. for overnight. The reaction mixture is then cooled to room temperature, condensed, and treated with 75 mL ethyl acetate. The reaction mixture is partitioned between ethyl acetate and aqueous layer. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 10% to 80% to afford 5-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine: 1H NMR 400 MHz (d6-DMSO) δ 8.72 (s, 1H), 7.53 (s, 1H), 6.90 (s, 1H), 5.26 (s, 1H), 2.57 (s, 3H), 2.08 (s, 3H); MS m/z 222.07 (M+1).

후처리

  1. temperatureThe reaction mixture is then cooled to room temperature
  2. customcondensed
  3. customThe reaction mixture is partitioned between ethyl acetate and aqueous layer
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product is purified by ISCO chromatography
  7. washeluting with ethyl acetate in hexanes from 10% to 80%

출처 및 근거

ORD 기록
ord-e8f9c9326c874781be6fe58dad94815f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202876B2

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