Sodium hydride → HCID 22466488, compound

Participants

Reaction Steps

A solution of 300 mg (1.31 mmol) of 2-(methylthio)-4-chloro-6-ethyl-1H-pyrrolo[2,3-d]pyrimidine in 10 mL of tetrahydrofuran (THF) was added to a 0° C. slurry of 377 mg (1.97 mmol) of 3-fluorobenzyl bromide and 55 mg (2.30 mmol) of sodium hydride in 10 mL of THF. The reaction was allowed to warm to ambient temperature and stirred for 16 hours. The reaction was quenched by the addition of 15 mL of brine. The organic phase was dried with sodium sulfate and concentrated to an oil. The product precipitated upon addition of hexanes to provide 384 mg (87%) of 2-(methylthio)-4-chloro-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidine as a light tan solid. nmr (300 MHz, CDCl3) δ1.11 (t, 3H), 2.58 (s, 3H), 2.59 (q, 2H), 5.39 (s, 2H), 6.29 (s, 1H), 6.75 (d, 1H), 6.85 (d, 1H), 6.96 (dt, 1H), 7.26 (dt, 1H)

Provenance & Evidence