Sodium Methoxide → 7-Amino-3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidin-2-one
Reaction equation
[NH2:1][C:2]1[C:3]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:34][C@H:33]([CH2:35][O:36]C(=O)C4C=CC=CC=4)[C@@H:23]([O:24]C(=O)C4C=CC=CC=4)[C@H:13]3[O:14]C(=O)C3C=CC=CC=3)[C:4]=2[N:5]=[CH:6][N:7]=1.C[O-].[Na+]>CO>[NH2:1][C:2]1[C:3]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:23]([OH:24])[C@H:13]3[OH:14])[C:4]=2[N:5]=[CH:6][N:7]=1Participants
4
Procedure
Compound 32 (0.76 g, 1.2 mmol) was deblocked in the same manner as described for 31 above using sodium methoxide (200 mg, 3.7 mmol) in dry MeOH (50 mL). The title compound (34) was obtained (0.12, 32%) after crystallization from water: mp 248°-250° C.: UV λmax (pH 1) 222 nm (ε 35100), 265 (14,300), 290 (11,400): UV λmax (pH 7, 11) 215 nm (ε 45000), 262 (13,200): 1H NMR (DMSO-d6) δ 5.91 (d, J=5.43 Hz, 1H, C1,H), 7.44 (b, 1H, NH2), 8.22 (s, 1H, C5H), and other sugar protons. Anal. Calcd. for C10H12N4O5S: C, 40.00: H, 4.03: N, 18.66: S, 10.68. Found: C, 39.80: H, 3.99: N, 18.39: S, 10.57.