Sodium Nitrite → 3-beta-D-Ribofuranosylthiazolo[4,5-d]pyrimidine-2,5,7(4H,6H)-trione

HRID 2248931Notes

Reaction equation

HRID 2248931 reaction equation
N[C:2]1[NH:3][C:4](=[O:21])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:6]=2[N:7]=1.N([O-])=[O:23].[Na+]>C(O)(=O)C.O>[C@@H:12]1([N:8]2[C:6]3[NH:7][C:2](=[O:23])[NH:3][C:4](=[O:21])[C:5]=3[S:10][C:9]2=[O:11])[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]1[OH:14]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 135409474Isatoribine Anhydrous

Product 1

HCID 145057353-beta-D-Ribofuranosylthiazolo[4,5-d]pyrimidine-2,5,7(4H,6H)-trione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of 7 (0.76 g, 2.4 mmol) in glacial acetic acid (150 mL) was added dropwise a solution of sodium nitrite (1.5 g, 21.7 mmol) in water (15 mL) with stirring. After 30 min the suspension became clear and stirring was continued at room temperature overnight. The white solid which had separated was filtered, washed with cold water and dried. Recrystallization from hot water gave fine colorless crystals of 8: yield 0.3 g, 40%: mp 250° C. dec.: UV λmax (pH 1) 293 nm (ε 5500): UV λmax (pH 7) 212 nm (ε 14,200), 301 (6100): UV λmax (pH 11) 204 nm (ε 21,900), 301 (5600). Anal Calcd. for C10H11N3O7S: C, 37.86: H, 3.49: N, 13.24: S, 10.10. Found: C, 37.81: H, 3.42: N, 13.01: S, 10.01.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customThe white solid which had separated
  4. filtrationwas filtered
  5. washwashed with cold water
  6. customdried
  7. customRecrystallization from hot water
  8. customgave fine colorless crystals of 8

Sources & evidence

ORD record
ord-b280bd1b54a94b3fa77843820e398502
Source dataset
uspto-grants-1991_08
Patent number
US05041426

Reaction notes

Loading…