Sodium Carbonate → (2-Chloro-6-methyl-pyrimidin-4-yl)-(5-methyl-3H-pyrazol-3-yl)-amine

HRID 2105237Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[N:13]=[C:12](Cl)[CH:11]=[C:10]([CH3:15])[N:9]=1.[NH2:16][C:17]1[NH:21][N:20]=[C:19]([CH3:22])[CH:18]=1>C(O)C>[Cl:7][C:8]1[N:13]=[C:12]([NH:16][C:17]2[CH:18]=[C:19]([CH3:22])[NH:20][N:21]=2)[CH:11]=[C:10]([CH3:15])[N:9]=1

Participants

Conditions

Temperature: 42 °C

Procedure

Solid sodium carbonate (1.2 g, 11.3 mmol) was added to a solution of 2,4-dichloro-6-methylpyrimidine (1.7 g, 10.3 mmol) and 5-amino-3-methyl-1H-pyrazole (1.0 g, 10.3 mmol) in dry ethanol (50 ml) and the mixture heated and stirred at 42° C. for 3 days. The mixture was allowed to cool, the insoluble material was removed by filtration and the filter pad washed with ethanol (10 ml). The volatiles were removed from the filtrate by evaporation, keeping the bath temperature below 40° C. The residue was immediately purified by chromatography on silica gel eluting with methanol/DCM (5:95 increasing in polarity to 20:80) to give the title compound (758 mg, 33%) as a white solid.

Workup

temperaturethe mixture heated
temperatureto cool
customthe insoluble material was removed by filtration
washthe filter pad washed with ethanol (10 ml)
customThe volatiles were removed from the filtrate by evaporation
customthe bath temperature below 40° C
customThe residue was immediately purified by chromatography on silica gel eluting with methanol/DCM (5:95 increasing in polarity to 20:80)

Sources & evidence

ORD record: ord-a1f725c31581448f91e7ab876066baf8
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579349B2

Reaction notes

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