Triethylamine → HCID 58338021, compound

Participants

Reaction Steps

[2-(2-Fluoro-4-methoxyphenyl)-ethyl]-thiazolo[5,4-d]pyrimidin-7-ylamine 7-Chlorothiazolo[5,4-d]pyrimidine (564 mg, 3.3 mmol) was dissolved with magnetic stirring in DMF (10 mL) in a 25 mL round bottom flask equipped with a dry nitrogen line at 25° C. To the solution was added 2-(2-fluoro-4-methoxyphenyl)-ethylamine hydrochloride (700 mg, 3.4 mmol) and triethylamine (Et3N, 1.19 mL, 8.5 mmol). After stirring overnight, the reaction was diluted with saturated (satd) aqueous (aq) ammonium chloride (NH4Cl; 10 mL) and concentrated in vacuo. The residue was partitioned between H2O (10 mL) and EtOAc (3×10 mL). The pooled organic fractions were diluted with pentane (15 mL), washed with H2O (10 mL) and brine (10 mL). After drying (sodium sulfate; Na2SO4), the solution was filtered through a SiO2/cotton plug, and concentrated in vacuo to provide 0.38 g. The aqueous fractions were washed with additional EtOAc, dried (Na2SO4) and filtered through a SiO2/cotton plug, and concentrated in vacuo to provide an additional 0.23 g of crude product. The two fractions were combined and purified by flash column chromatography (SiO2, 0-100% EtOAc/hexane). The appropriate fractions were pooled to afford [2-(2-fluoro-4-methoxyphenyl)-ethyl]-thiazolo[5,4-d]pyrimidin-7-ylamine (Compound 55; 230 mg) as a gold solid: mp 136-139° C.; 1H NMR (DMSO-d6) δ 9.21 (s, 1H), 8.39 (s, 1H), 8.32 (br m, 1H), 7.19 (t, J=8.7 Hz, 1H), 6.77-6.67 (m, 2H), 3.74-3.67 (m, 5H), 2.89 (t, J=7.4 Hz, 3H); ESIMS m/z 305.5 ([M+H]+).

Provenance & Evidence