2,4-Dichloropyrimidine → 2-chloro-N-(5-(difluoromethyl)-1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 475310Notes

Reaction equation

HRID 475310 reaction equation
[F:1][CH:2]([F:9])[C:3]1[NH:7][N:6]=[C:5]([NH2:8])[CH:4]=1.[Cl:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[CH:13][N:12]=1.CCN(C(C)C)C(C)C>CCO>[Cl:10][C:11]1[N:16]=[C:15]([NH:8][C:5]2[CH:4]=[C:3]([CH:2]([F:9])[F:1])[NH:7][N:6]=2)[CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 508966613-(difluoromethyl)-1H-pyrazol-5-amine

Product 1

HCID 866947612-chloro-N-(5-(difluoromethyl)-1H-pyrazol-3-yl)pyrimidin-4-amineYield 7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-(difluoromethyl)-1H-pyrazol-3-amine (8.0 g, 60.1 mmol) in EtOH (350 mL) was added 2,4-dichloropyrimidine (10.7 g, 72.1 mmol) and DIPEA (10.9 g, 84.1 mmol). The reaction was stirred at 70° C. for 30 h. The reaction mixture was concentrated in vacuo. The crude product was purified by SiO2 chromatography to afford 2-chloro-N-(5-(difluoromethyl)-1H-pyrazol-3-yl)pyrimidin-4-amine (1.00 g, 7%). 1H NMR (400 MHz, DMSO) δ 13.23 (d, J. 68.6 Hz, 1H), 10.57 (s, 1H), 8.22 (d, J=4.9 Hz, 1H), 7.08 (m, 3H). MS (ESI) m/z: 246.0 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-cadbccbe204b40109d104228f0e13094
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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