Allyl bromide → HCID 86667335, compound

Participants

Reaction Conditions

Reaction Steps

To 2-chloro-5,7-dimethyl-4-morpholino-5H-pyrrolo[3,2-d]pyrimidin-6(7H)-one (92.0 mg, 0.32 mmol) in anhydrous THF (5 mL) under N2 at −78° C. was added dropwise 1.0 M lithium hexamethyldisilazide in THF (0.65 mL, 0.65 mmol). The reaction mixture was stirred at −78° C. under N2 for 60 minutes. Allyl bromide (0.062 mL, 0.72 mmol) dissolved in 0.5 mL of THF was added, and the reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography eluted with 10 to 100% ethyl acetate/heptane gave 84.3 mg (80.3%) of 7-allyl-2-chloro-5,7-dimethyl-4-morpholino-5H-pyrrolo[3,2-d]pyrimidin-6(7H)-one. MS(ESI) m/z: 323.1 [M+1]+.

Provenance & Evidence