Sodium Methoxide → 7-Amino-3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidin-2-one

HRID 1638538Notes

Reaction equation

HRID 1638538 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]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 145057657-Amino-3-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)thiazolo[4,5-d]pyrimidin-2-one

Product 1

HCID 145057697-Amino-3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (ε35100), 265 (14300), 290 (11400): UV λmax (pH 7, 11) 215 nm (ε45000), 262 (13200): 1H NMR (DMSO-d6) δ5.91 (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. ##STR7##

Sources & evidence

ORD record
ord-cf289d55b1314c0d98df43ae2ac5d114
Source dataset
uspto-grants-1989_11
Patent number
US04880784

Reaction notes

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