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

HRID 1638527Notes

Reaction equation

HRID 1638527 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 (ε5500): UV λmax (pH 7) 212 nm (ε14200), 301 (6100): UV λmax (pH 11) 204 nm (ε21900), 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-a9cb9d86b2d64cd9a4b875c7f715ecea
Source dataset
uspto-grants-1989_11
Patent number
US04880784

Reaction notes

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