Methyl iodide → 5-Chloro-1-methyl-1H-pyrazolo[4,3-D]pyrimidine

HRID 243337Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[N:9]=[CH:10][C:11]2[NH:16][N:15]=[CH:14][C:12]=2[N:13]=1.IC>O1CCCC1>[Cl:7][C:8]1[N:9]=[CH:10][C:11]2[N:16]([CH3:1])[N:15]=[CH:14][C:12]=2[N:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium t-butoxide (1.68 g, 14.67 mmol, 1.14 equiv) was added to a solution of 5-chloro-1H-pyrazolo[4,3-d]pyrimidine (2.1 g, 12.91 mmol, 1.00 equiv, 95%) in tetrahydrofuran (50 mL) at 0° C. After the reaction mixture was stirred at 0° C. for 30 min, iodomethane (3 g, 20.71 mmol, 1.60 equiv, 98%) was added dropwise at 0° C. The resulting solution was stirred for 4.5 h at room temperature and then concentrated under vacuum. The residue was loaded onto a silica gel column and eluted with dichloromethane/ethyl acetate (10/1) to give 300 mg (14%) of 5-chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine as a white solid.

Workup

stirringThe resulting solution was stirred for 4.5 h at room temperature
concentrationconcentrated under vacuum
washeluted with dichloromethane/ethyl acetate (10/1)

Sources & evidence

ORD record: ord-2523d93b75e54bcd8bf8b688e04053c3
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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