Sodium Hydroxide → 4-chloro-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine

HRID 714775Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[NH:13][C:12](=O)[CH:11]=[CH:10][N:9]=2)[CH:4]=[N:3]1.P(Cl)(Cl)([Cl:17])=O.[OH-].[Na+]>C(#N)C>[Cl:17][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)[N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4(3H)-one (3.4 g) obtained in Step B in acetonitrile (35 mL) was added dropwise phosphorus oxychloride (3.2 mL), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was neutralized with 8M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated to give the title compound (3.3 g).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-f717a65933504a04a34e67b16b899f34
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

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