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

HRID 220084

反応式

HRID 220084 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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%

出典と根拠

ORDレコード
ord-e8f9c9326c874781be6fe58dad94815f
出典データセット
uspto-grants-2012_06
特許番号
US08202876B2

関連ノート

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