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

HRID 323859Notes

Reaction equation

HRID 323859 reaction equation
Cl.[CH2:2]([N:9]1[C:17]2[C:16](=[O:18])[NH:15][C:14](N)=[N:13][C:12]=2[N:11]=[CH:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N([O-])=[O:21].[Na+]>O.C(O)(=O)C>[CH2:2]([N:9]1[C:17]2[C:16](=[O:18])[NH:15][C:14](=[O:21])[NH:13][C:12]=2[N:11]=[CH:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 1356820512-Amino-7-benzyl-1,7-dihydro-6H-purin-6-one hydrochloride

Product 1

HCID 125005077-Benzyl-1H-purine-2,6(3H,7H)-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

35.9 g (0.13 mol) of 7-benzylguanine hydrochloride from stage a) were dissolved in a mixture of 90 ml of water and 807 ml of glacial acetic acid and heated to 100° C. After cooling to 50° C., a solution of 35.88 g (0.52 mol) of sodium nitrite in 90 ml of water was added in one portion. After 16 hours at room temperature, the resulting precipitate was filtered off with suction, washed with water on the suction filter and dried.

Workup

  1. temperatureAfter cooling to 50° C.
  2. filtrationthe resulting precipitate was filtered off with suction
  3. washwashed with water on the suction
  4. filtrationfilter
  5. customdried

Sources & evidence

ORD record
ord-551dba0e031b4f2f9134e28d7e3c7d4b
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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