5-amino-3-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)thiazolo-[4,5-d]pyrimidine-2,7(6H)-dione → Isatoribine Anhydrous

HRID 1638526Notes

Reaction equation

HRID 1638526 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:45])[C:5]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:6]=2[N:7]=1.O(C)[Na]>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:45])[C:5]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:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 1360537475-amino-3-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)thiazolo-[4,5-d]pyrimidine-2,7(6H)-dioneHCID 178418582HCID 178418582, compound

Product 1

HCID 135409474Isatoribine Anhydrous

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6 (0.75 g, 1 mmol) in methanol (75 mL) was adjusted to pH 9 with NaOCH3 and stirred at room temperature for 16 h. The reaction mixture was evaporated to dryness and the residue was triturated with ether (2×75 mL). The ether insoluble solid was dissolved in water (15 mL) and acidified with acetic acid whereupon the crude product precipitated. Crystallization of this material from water gave a colorless powder: yield 0.31 g, 78%: mp 238° C. (decomp.): UV λmax (pH 1) 215 nm (ε2280), 245 (6900), 301 (8400): UV λmax (pH 7) 215 nm (ε22100), 245 (6900), 301 (8000): UV λmax (pH 11) 245 nm (ε5700), 291 (6000). NMR (DMSO-d6) δ5.79 (1H, d, J=5.32 Hz, C1, H), 6.90 (2H, s, NH2), 11.12 (1H, s, NH), and other sugar protons. Anal. Calcd. for C10H12N4O6S.H2O: C, 35.92: H, 4.22: N, 16.76: S, 9.59. Found: C, 35.82: H, 4.02: N, 16.92: S, 9.66.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was triturated with ether (2×75 mL)
  3. dissolutionThe ether insoluble solid was dissolved in water (15 mL)
  4. customprecipitated
  5. customCrystallization of this material from water
  6. customgave a colorless powder

Sources & evidence

ORD record
ord-f6a8303caa4146a2a7a287f94893b386
Source dataset
uspto-grants-1989_11
Patent number
US04880784

Reaction notes

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