Tetrahydrofuran → 4-Phthalimido-7-[3,5-di-o-(p-toluoyl)-2-c-methyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Tetrahydrofuran (5.4 L), sodium hydride (146 g of 60% dispersion in oil, unwashed), and N,N-dimethylacetamide (4 L) were charged to a 72 L flask and the suspension was cooled to 0° C. 4-Phthalimido-7H-pyrrolo[2,3-d]pyrimidine (3-2) (2.08 kg) was added to the reaction while maintaining the temperature below 25° C. N,N-Dimethylacetamide (1.4 L) was added followed by the solution of the epoxide (2.75 assay kg) in toluene from Step A, and the reaction mixture was heated at 50-90° C. for 9 h. After cooling to ambient temperature, ethyl acetate (19 L) and aqueous KH2PO4 (0.97 kg in 19 L of water) were added. The organic phase was washed with water. The resulting organic solution was solvent-switched to toluene by vacuum distillation (T<40° C.) to give a final volume of 10 L.

Provenance & Evidence