Sodium Nitrite → 7-Benzyl-1H-purine-2,6(3H,7H)-dione

HRID 2374299Notes

Reaction equation

HRID 2374299 reaction equation
N[C:2]1[NH:10][C:9]2[N:8]=[CH:7][N:6]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[C:4](=[O:18])[N:3]=1.N([O-])=[O:20].[Na+]>C(O)(=O)C.O>[CH2:11]([N:6]1[C:5]2[C:4](=[O:18])[NH:3][C:2](=[O:20])[NH:10][C:9]=2[N:8]=[CH:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 178508905HCID 178508905, compound

Product 1

HCID 125005077-Benzyl-1H-purine-2,6(3H,7H)-dioneYield 79.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 2-amino-7-benzyl-3,7-dihydro-6H-purin-6-one (25.0 g, 0.104 mol) in acetic acid (750.0 mL) and water (50.0 mL) at 55° C. was added a solution of sodium nitrite (28 g, 0.41 mol) in water (50 ml) dropwise. After the addition, the mixture was continued to stir for about 30 min until no starting material was left and then cooled to room temperature. The reaction mixture was concentrated to about ⅓ of its original volume, then diluted with 250 ml water. The precipitate formed was collected by filtration to provide the desired product (20 g, 79.7%). LCMS calculated for C12H11N4O2(M+H): 243.1; found: 243.1.

Workup

  1. additionAfter the addition
  2. waitwas left
  3. concentrationThe reaction mixture was concentrated to about ⅓ of its original volume
  4. additiondiluted with 250 ml water
  5. customThe precipitate formed
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-6da03d09c7754763bf58b0ea4c02a008
Source dataset
uspto-grants-2008_12
Patent number
US07462624B2

Reaction notes

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