N-tert-Butyl-7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-amine → HCID 58095024, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-Butyl-(7-chlorothiazolo[5,4-d]pyrimidin-2-yl)-amine (1.00 g, 4.12 mmol), 1-allyl-2-[3-(2,4-dichlorophenyl)-5-(tributylstannyl)-2-thienyl]-1H-imidazole (1.71 g, 2.75 mmol) and DMF (23 mL) was stirred and degassed with vacuum. The atmosphere was replaced with nitrogen and then bis(triphenylphosphine)palladium(II) chloride (96.4 mg, 0.137 mmol) was added to the mixture. The orange solution was heated at 100° C. for 3 hours and the mixture was allowed to cool to rt. Column chromatography was performed to yield the title compound (1.12 g, 75%) as a pale yellow solid. LCMS: (FA) ES+ 541, 543. 1H NMR (400 MHz, d6-DMSO) δ; 8.73 (bs, 1H), 8.65 (bs, 1H), 8.56 (bs, 1H), 7.75 (d, J=2.5 Hz, 1H), 7.38 (dd, J=8.5, 2.5 Hz, 1H), 7.21 (d, J=1.3 Hz, 1H), 7.12 (d, J=8.5 Hz, 1H), 7.05 (d, J=1.3 Hz, 1H), 5.64-5.55 (m, 1H), 5.06-5.03 (m, 1H), 4.84-4.79 (m, 1H), 4.31-4.27 (m, 2H), 1.49 (s, 9H).

Provenance & Evidence