Sodium Hydroxide → HCID 66779840, compound

Participants

Reaction Steps

Isopropylmagnesium chloride (1.679 mL, 3.36 mmol) was added to a suspension of 2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (0.8 g, 3.36 mmol) in Tetrahydrofuran (THF) (30 mL) at 0° C. LiHMDS (3.36 mL, 3.36 mmol) was added. The ice bath was removed. The reaction mixture was stirred at RT for 30 min, cooled down to 0° C. 1-(Bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (1 g, 3.95 mmol) was added. The reaction mixture was heated at 60 C overnight. LCMS showed very clean reaction. NaOH (1.12 mL, 6.72 mmol, 6N) was added. The resulting mixture was heated at 60° C. for 1 hr (MeOH may be added to accelerate the reaction). LCMS showed the hydrolysis was almost complete. Water was added, creamy-colored solid was formed, filtered, rinsed with water, and dried under high vacuum at 50° C. to give 1.58 g of product, which may contain inorganic salt.

Provenance & Evidence