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

HRID 2248942Notes

Reaction equation

HRID 2248942 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 (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.

Sources & evidence

ORD record
ord-28a38142e18342e0aff4f3febbc99bc3
Source dataset
uspto-grants-1991_08
Patent number
US05041426

Reaction notes

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