Cesium carbonate → HCID 59271805, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the methyl 2-{1-[(tert-butoxycarbonyl)(methyl)amino]-5-[(methylsulfonyl)oxy]hexyl}-5,6-bis[(methylsulfonyl)oxy]pyrimidine-4-carboxylate (62 g, 98 mmol) and cesium carbonate (64 g, 196 mmol) in DMF (400 mL) was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and then cooled further to 0° C. More cesium carbonate (60 g) was added followed by MsCl (10 mL) and stirring continued for 1 hour. The reaction mixture was filtered to remove solids and the solids were then washed with methylene chloride until the filtrate ran clear. The filtrate was then stripped and finally under high vacuum at 35° C. to remove the DMF. The thick dark red residual sludge was diluted with ether and filtered. The filter cake was washed with ether. The resulting cream colored solid was dissolved in methylene chloride and washed once with cold half-saturated brine and the solution dried over sodium sulfate. Filtration and concentration gave the racemic trans diastereomer as determined by NMR and LC-MS: 1H NMR (400 MHz, CDCl3) δ 5.74 (m, 1H), 5.41 (dd, J=1.6, 13.5 Hz, 1H), 3.92 (s, 3H), 3.50 (s, 3H), 2.95 (s, 3H), 1.60-2.94 (m, 6H), 1.57 (d, J=7.3 Hz, 3H), 1.44 (s, 9H). ES MS M+1=460.12.

Provenance & Evidence