Potassium Carbonate → 5-Amino-7-cyclopropylmethoxy-3-beta-D-ribofuranosyl-thiazolo [4,5-d]pyrimidin-2-one

Participants

Reaction Steps

To a suspension of 62 (570 mg, 1.18 mmol) in MeOH was added K2CO3 (50 mg, 0.36 mmol) at room temperature. The reaction mixture was stirred 1 h, concentrated, partitioned between 20% IPA-CHCl3 and water, and then triturated with Et2O to afford 128 mg (29%) of 63 as a white solid: 1H (400 MHz, d6-DMSO) δ 6.86 (s, 2H), 5.85 (d, J=5.1 Hz, 1H), 5.27 (d, J=5.5 Hz, 1H), 4.96 (d, J=5.5 Hz, 1H), 4.77 (q, J=5.5 Hz, 1H), 4.66 (t, J=5.9 Hz, 1H), 4.18 (dd, J=7.3, 1.1 Hz, 1H), 4.09 (q, J=5.5 Hz, 1H), 3.75 (q, J=5.1 Hz, 1H), 3.39-3.60 (m, 2H), 1.20-1.27 (m, 1H), 0.53-0.57 (m, 2H), 0.31-0.34 (m, 2H); MS (+)-ES [M+H]+ m/z 371. Elemental Analysis calc'd for C14H18N4O6S: C, 45.40; H, 4.90; N, 15.13; S, 8.66. Found: C, 44.98; H, 4.92; N, 14.92; S, 8.49.

Provenance & Evidence