Triethanolamine → (1S,2S,3R,5S)-3-(7-Chloro-5-(Propylthio)-3H-[1,2,3]Triazolo[4,5-d]Pyrimidin-3-Yl)-5-(2-Hydroxyethoxy)Cyclopentane-1,2-Diol

Participants

Reaction Conditions

Reaction Steps

A mixture of (1S,2S,3R,5S)-3-amino-5-(2-hydroxyethoxy)cyclopentane-1,2-diol (OLA; 0.89 g, 5 mmol), 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (CLINA; 1.19 g, 5 mmol) and triethanolamine (1.49 g, 10 mmol) was stirred neat for 24 h at 90° C. After cooling to ambient temperature, the viscous reaction mixture was dissolved by the addition of acetic acid (3 mL). While maintaining the reaction temperature at 15-20° C. there was added sodium nitrite (0.38 g, 5.5 mmol) and the reaction mixture left stirring for 12 h. The reaction mixture was diluted with ethyl acetate (35 mL), washed with water (2×25 mL) and evaporated under reduced pressure. The crude product was triturated in hexane (20 mL) and filtered to give CLTOL as an off-white powder (1.61 g, 83% yield): 13C NMR (CDCl3, 125 MHz) δ13.4, 22.0, 33.5, 33.7, 61.75, 61.77, 71.1, 74.9, 75.4, 82.0, 131.8, 150.7, 152.9, 171.8.

Provenance & Evidence