Cyclopropanecarbonyl chloride → HCID 178517406, compound

Participants

Reaction Steps

To a solution of 4-amino-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (0.15 g, 0.657 mmol) in Dichloromethane (DCM) (2 ml) at 0° C. was added cyclopropanecarbonyl chloride (0.075 ml, 0.821 mmol) dropwise. The mixture was stirred at room temperature overnight, and then concentrated. To the resulting residue was added ethanol (1 mL) and 6N NaOH (0.8 mL). The mixture was stirred at room temperature for 3 h, and then acidified with 6N HCl (0.7 mL) to pH ˜5. The precipitate was collected, rinsed with water, and dried in vacuo to furnish crude 5-cyclopropyl-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (90 mg, 49%); LC/MS: MS (ES) m/e 279 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.06 (m, 4H), 1.95 (ddd, J=10.6, 2.0, 1.8 Hz, 1H) 3.53-3.59 (m, 4H) 3.68-3.76 (m, 4H) 12.56 (br, s, 1H).

Provenance & Evidence