3-cyclopropyl-1H-pyrazol-5-amine → 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[C:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][N:3]=1.[CH:15]1([C:18]2[NH:22][N:21]=[C:20]([NH2:23])[CH:19]=2)[CH2:17][CH2:16]1>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:23][C:20]2[CH:19]=[C:18]([CH:15]3[CH2:17][CH2:16]3)[NH:22][N:21]=2)[C:5]([C:9]#[C:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][N:3]=1Participants
4
Procedure
A mixture of 2,4-dichloro-5-((trimethylsilyl)ethynyl)pyrimidine (1.0 g, 4.1 mmol, 1.0 eq) and 5-cyclopropyl-1H-pyrazol-3-amine (756 mg, 6.2 mmol, 1.5 eq) in EtOH (4 ml) was stirred at room temperature for 2 h. The mixture was purified by silica gel column chromatography (PE/EtOAc=5:1 to 2:1) to afford 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine (900 mg, 66%).