Formamide → HCID 66780007, compound

Participants

Reaction Conditions

Reaction Steps

4-[(3-chloro-2-methylphenyl)methyl]-5-(methylthio)-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (500 mg, 1.182 mmol) in formamide (8 ml, 201 mmol) was heated at 192° C. and stirred for 1 h. The temperature was increased to 198° C. and stirring was continued for additional 3 h. After cooling, water was added in and the precipitate was collected, washed with water, then Et2O and dried to give 437 mg of crude. The material was purified by prep HPLC on a Kromasil Silica 5u 60 A 21×250 mm column, eluting with 95:5—CHCl3:CH3OH (2M NH3) at 20 mL/min and collecting fraction at about 7.2 min. 5-amino-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (151 mg, 0.380 mmol, 32.1% yield) was obtained from the crude as an off white powder. LC/MS (ES) m/z=392.1 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 7.36 (d, J=7.83 Hz, 1H), 7.16 (t, J=7.96 Hz, 1H), 6.97 (s, 2H), 6.51 (d, J=7.58 Hz, 1H), 5.31 (s, 2H), 3.61-3.70 (m, 4H), 3.42 (t, J—=4.80 Hz, 4H), 2.38 (s, 3H)

Provenance & Evidence