Acetic Acid → 1-beta-D-arabinofuranosyl-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one

HRID 1447001Notes

Reaction equation

HRID 1447001 reaction equation
[C@@H:1]1([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14](N)[C:13]=3[N:12]=[CH:11]2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].C(O)(=[O:22])C.N([O-])=O.[Na+].NC(N)=O>O>[C@@H:1]1([N:10]2[C:18]3[CH:17]=[CH:16][NH:15][C:14](=[O:22])[C:13]=3[N:12]=[CH:11]2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1176UreaHCID 127697241-beta-d-Arabinofuranosyl-1H-imidazo[4,5-c]pyridin-4-amineHCID 23668193Sodium Nitrite

Product 1

HCID 127994161-beta-D-arabinofuranosyl-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.5 g of 1-β-D-arabinofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine, 6 ml of acetic acid, 150 ml of water, and 2.67 g of sodium nitrite is kept at ambient temperature for 8 hours, treated with 2.4 g of urea, and then with 50 ml of wet Dowex 50 1×8 (H+), and concentrated to dryness in vacuo. The residue is coevaporated several times with xylenes and then recrystallized from water to provide 1-β-D-arabinofuranosyl-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one.

Workup

  1. concentrationwith 50 ml of wet Dowex 50 1×8 (H+), and concentrated to dryness in vacuo
  2. customrecrystallized from water

Sources & evidence

ORD record
ord-aa56018e329a454ea1a18174212e6817
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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