Acetic Acid → 7-beta-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 1904114Notes

Reaction equation

HRID 1904114 reaction equation
[C@@H:1]1([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18](N)[C:13]=3[CH: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:14]3[N:15]=[CH:16][NH:17][C:18](=[O:22])[C:13]=3[CH: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 30079187-beta-D-Arabinofuranosyl-7H-pyrrolo(2,3-d)pyrimidin-4-amineHCID 23668193Sodium Nitrite

Product 1

HCID 1357068257-beta-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of one g of 7-β-D-arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine, 4.3 ml of glacial acetic acid, 50 ml water, and 2.67 g of sodium nitrite is heated at 75° C. for one hour, cooled, and treated with 2.1 g of urea. The solution is evaporated in vacuo and the resulting residue is dissolved in water and treated with 15 ml of wet Dowex 50×8 (in hydrogen form). The resin is filtered and washed with water. The filtrate is treated with charcoal, filtered and evaporated in vacuo. The residue is recrystallized from water to provide 0.75 g of pure 7-β-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one.

Workup

  1. temperaturecooled
  2. customThe solution is evaporated in vacuo
  3. dissolutionthe resulting residue is dissolved in water
  4. additiontreated with 15 ml of wet Dowex 50×8 (in hydrogen form)
  5. filtrationThe resin is filtered
  6. washwashed with water
  7. additionThe filtrate is treated with charcoal
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue is recrystallized from water

Sources & evidence

ORD record
ord-649b9343b6e04690b54ccf7891d69440
Source dataset
uspto-grants-1984_03
Patent number
US04439604

Reaction notes

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