Ammonia → 2,5,6-Triamino-4-Benzyloxypyrimidine

HRID 1838962Notes

Reaction equation

HRID 1838962 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([N:16]=O)=[C:4]([NH2:18])[N:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].N>O>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH2:16])=[C:4]([NH2:18])[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24489Sodium Dithionite2×HCID 1810292,4-Pyrimidinediamine, 5-nitroso-6-(phenylmethoxy)-

Product 1

HCID 98160442,5,6-Triamino-4-Benzyloxypyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2,6-diamino-4-benzyloxy-5-nitrosopyrimidine (0.3 g, 1.28 mmol) in water (10 ml) at 50° C. was added sodium dithionite (0.48 g, 2.76 mmol) in portions over 5 h. The reaction mixture was stirred at room temperature overnight, heated again to 50° C. and a further quantity of sodium dithionite (0.4 g) was added. After stirring for a further 12 h, the reaction mixture was cooled to room temperature, and the solution was adjusted to pH 7 with aqueous ammonia solution (0.2 ml). The resultant fine yellow solid which deposited was collected, washed with water and recrystallised from hot water (0.11 g, 35%), m.p. 130-135° C.; νmax/cm−1 3394 (NH2), 3033 (C6H5); δH (200 MHz, d6-DMSO) 5.36 (2H, s, OCH2), 5.40 (2H, s, NH2), 5.81 (2H, s, NH2), 7.39-7.56 (5H, m, C6H5).

Workup

  1. temperatureheated again to 50° C.
  2. stirringAfter stirring for a further 12 h
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customThe resultant fine yellow solid which deposited was collected
  5. washwashed with water
  6. customrecrystallised from hot water (0.11 g, 35%), m.p. 130-135° C.

Sources & evidence

ORD record
ord-12a945fa169443b79e976dba34381da4
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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