Reaction #88479

Reaction equation

[2-(2,6-dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine

morpholine

→

title compound

Yield 77.0%

[2-(2,6-Dichloro-benzyl)-5-morpholin-4-yl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine

Yield 77.0%

Solvents

tert-amyl alcohol

Conditions

Workup

1. 1
   Temperaturethe solution was cooled
2. 2
   Otherpurified by preparative reverse-phase HPLC

Procedure

To a mixture of [2-(2,6-dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine (49 mg, 0.1 mmol) in tert-amyl alcohol (2 mL) was added morpholine (24 mg, 0.3 mmol). The resulting mixture was heated to 130° C. in a sealed tube. After 12 h, the solution was cooled and purified by preparative reverse-phase HPLC to afford the title compound as a colorless solid (37 mg, 77%). MS (ESI): mass calcd. for C23H18Cl2F3N5OS, 539.0; m/z found, 540.0 [M+H]+. 1H NMR ((CD3)250): 10.14 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.70 (d, J=8.6 Hz, 2H), 7.61 (d, J=8.1 Hz, 2H), 7.49-7.42 (m, 1H), 4.69 (s, 2H), 3.66 (s, 8H).

Source