1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-chloro-7-(3,3-difluorocyclobutyl)-2-(methylsulfanyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{4-chloro-6-[(3,3-difluorocyclobutyl)amino]-2-(methylsulfanyl)pyrimidin-5-yl}ethyl methanesulfonate (922 mg, 2.38 mmol) in DMF (23 mL) was added DBU (0.725 mL, 4.75 mmol). The mixture was stirred at 80° C. for 1 h, whereupon the reaction mixture was diluted with EtOAc (40 mL), washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and concentrated under reduced pressure to give 649 mg (94%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 4.44-4.33 (m, 1 H), 3.75 (t, J=8.5 Hz, 2 H), 3.13-2.99 (m, 2 H), 2.98-2.92 (m, 2 H), 2.91-2.81 (m, 2 H), 2.42 (s, 3 H). m/z (APCI+) for C11H12ClF2N3S 292.0 (M+H)+.

Provenance & Evidence