Acetic Acid → 2-(2-Allyloxyphenyl)-4,5-diaminopyrimid-6-one

HRID 1288270Notes

Reaction equation

HRID 1288270 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:12][C:13](=[O:20])[C:14]([N:18]=O)=[C:15]([NH2:17])[N:16]=1)[CH:2]=[CH2:3].C(N(CC)CC)C.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(O)(=O)C>O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:12][C:13](=[O:20])[C:14]([NH2:18])=[C:15]([NH2:17])[N:16]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 24489Sodium DithioniteHCID 1363546152-(2-Allyloxyphenyl)-4-amino-5-nitrosopyrimid-6-one

Product 1

HCID 1360237872-(2-Allyloxyphenyl)-4,5-diaminopyrimid-6-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-Allyloxyphenyl)-4-amino-5-nitrosopyrimid-6-one (6.3 g.) was suspended in a solution of triethylamine (15 ml.) in water (250 ml.). Sodium dithionite (12 g.) was added in portions with stirring at room temperature. The temperature of the mixture was then raised to 60° C., and it was stirred at this temperature for a further 20 minutes. The pH of the mixture was adjusted to 7 by the addition of glacial acetic acid, and the mixture cooled in ice/water. The solid was filtered off and washed with water to give 2-(2-allyloxyphenyl)-4,5-diaminopyrimid-6-one (5.1 g.), m.p. 127°-130° C.

Workup

  1. temperatureThe temperature of the mixture was then raised to 60° C.
  2. stirringit was stirred at this temperature for a further 20 minutes
  3. filtrationThe solid was filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-944bb8efc4e444de95138e12ee6b9149
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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