3-cyclopropyl-1H-pyrazol-5-amine → HCID 58169139, compound

HRID 1484913Notes

Reaction equation

HRID 1484913 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]=1

Participants

4

Reactant 2

HCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 210809892,4-Dichloro-5-((trimethylsilyl)ethynyl)pyrimidine

Product 1

HCID 58169139HCID 58169139, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%).

Workup

  1. customThe mixture was purified by silica gel column chromatography (PE/EtOAc=5:1 to 2:1)

Sources & evidence

ORD record
ord-7ae1a8b61ca1488c99b7f8f722682d9b
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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