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

HRID 220084

Reaction equation

HRID 220084 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

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).

Workup

  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%

Sources & evidence

ORD record
ord-e8f9c9326c874781be6fe58dad94815f
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Linked notes

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