N,N-Dimethylaniline → 5,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-methyl-4H-thiazolo[5,4-d]pyrimidine-5,7-dione (7.5 g, 0.041 mol) in N,N-dimethylaniline (3.7 mL, 0.029 mol) was added phosphorous oxychloride (38.0 mL, 0.410 mol) and the mixture heated at 130° C. for 4 h. The resulting black solution was cooled to RT, then carefully quenched with crushed ice and H2O, before being extracted with EtOAc. The organic layer was isolated, dried (MgSO4) and concentrated in vacuo to give a yellow solid. The solid was dissolved in DCM, then washed with an aqueous solution of NaHCO3 followed by brine, dried (Na2SO4) and concentrated in vacuo to give the title compound as a pale yellow solid (4.90 g, 54%).

Provenance & Evidence