2-Chloro-4,6-dimethylpyrimidine → N,N-Dimethyl-6-[(1S,6R)-8-{[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]oct-3-yl]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of Intermediate 12 (50 mg, 0.17 mmol), 2-chloro-4,6-dimethylpyrimidine (24 mg, 0.17 mmol) and DIPEA (0.87 mL, 0.5 mmol) in ACN (1 mL) was heated in the microwave at 200° C. for 2 h. The mixture was concentrated in vacuo and chromatography (Hex to 100% EtOAc/Hex) to afford the desired product as a pale yellow foam (39 mg, 55%). MS (ESI) mass calculated for C22H25N7O2, 419.2; m/z found, 420.2. 1H NMR (500 MHz, CDCl3): 8.15 (s, 1H), 8.12-8.04 (m, 1H), 7.59-7.50 (m, 2H), 7.25-7.17 (m, 1H), 5.22 (s, 1H), 4.44-4.33 (m, 2H), 4.11-3.99 (m, 1H), 3.94-3.73 (m, 2H), 3.68-3.60 (m, 1H), 3.11-3.05 (m, 6H), 3.02-2.86 (m, 2H), 2.45-2.42 (m, 3H), 2.22-1.97 (m, 2H).

Provenance & Evidence