Hydrochloric Acid → (1R,2S,3R,5R)-3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Participants

Reaction Steps

A suspension of crude (1R,2S,3R,5R)-3-((6-chloro-5-(2,2-diethoxyethyl)pyrimidin-4-yl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diol in 1,4-dioxane (160 mL) was treated with a 1 M aqueous solution of HCl (30 mL, 30 mmol) and stirred at RT for 69.5 h; HPLC indicated clean conversion to one product, LC MS showed mass for desired product. The reaction mixture was neutralized with concentrated aqueous NH4OH (to pH 7) and the volatiles were removed in vacuo to afford a brown slurry, which was carried on without further purification: MS (ESI+) for C12H14ClN3O3 m/z 284.1 (M+H)+; MS (ESI−) for C12H14ClN3O3 m/z 282.2 (M−H)−, 328.2 (M+HCO2)−; HPLC purity >95% (ret. time, 1.947 min). Variation on route from J. Med. Chem. 10, 665 (1967).

Provenance & Evidence