Potassium Carbonate → Cis-Cyclopentyl[1-(2-amino-6-chloro-4-pyrimidinyl)-6-methyl-3-piperidinyl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-cyclopentyl[6-methyl-3-piperidinyl]carbamate (107 mg, 0.473 mmol) in ethanol (3 mL) were added 4,6-dichloro-2-pyrimidinamine (116 mg, 0.709 mmol) and K2CO3 (98 mg, 0.709 mmol) in a 5 mL sealable vial. The solution was capped and heated at 100° C. overnight. The reaction was then check with LCMS and was not complete. Additional 4,6-dichloro-2-pyrimidinamine (30 mg) and K2CO3 (50 mg) were added and the resulting mixture was heated overnight. The reaction was concentrated, then 5 mL of DMF were added. Some solids were not soluble. Water (10 mL) was added, and the resulting mixture was extracted 3× with EtOAc. The organics were combined, washed with brine, dried over MgSO4, filtered and concentrated. The clear oil was then purified on Biotage SNAP 10 g column with gradient of 0 to 50% EtOAc in hexane over 30 minutes to afford the title compound (135 mg) as a clear oil. LC-MS (ES) m/z=354 [M+H]+.

Provenance & Evidence