Hydrochloric Acid → 4-[2-(Thiazolo[5,4-d]pyrimidin-7-ylamino)-ethyl]-phenol

Participants

Reaction Conditions

Reaction Steps

7-Chlorothiazolo[5,4-d]pyrimidine (2.71 grams (g), 15.7 millimoles (mmol)) and tyramine (2.16 g, 15.7 mmol) were dissolved with magnetic stirring in N,N-dimethylformamide (DMF; 20 milliliters (mL)) in a 100 mL round bottom flask equipped with a reflux condenser and a dry nitrogen line at 25° C. To the solution was added potassium carbonate (K2CO3; 6.0 g, 43.4 mmol), and the mixture was heated at 100° C., then cooled to 25° C., and stirred overnight. The reaction was diluted with water (H2O; 150 mL), and then treated with 2 N hydrochloric acid (HCl) to adjust the pH to 6. The aqueous layer was washed repeatedly with EtOAc, and the pooled organic fractions were filtered and concentrated in vacuo to provide 4-[2-(thiazolo[5,4-d]pyrimidin-7-ylamino)-ethyl]-phenol (Compound 3; 1.0 g) as an amber powder: mp 161-168° C.; 1H NMR (DMSO-d6) δ 9.24 (s, 1H), 9.18 (s, 1H), 8.42 (s, 1H), 8.29 (br s, 1H), 7.04 (d, J=8.0 Hz, 2H), 6.67 (d, J=8.3 Hz, 2H), 3.65 (m, 2H), 2.81 (m, 2H); ESIMS m/z 273.1 ([M+H]+).

Provenance & Evidence