Acetic Acid → 2,4-Pyrimidinediamine, 5-nitroso-6-(phenylmethoxy)-

HRID 260147Notes

Reaction equation

HRID 260147 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.C(O)(=O)C.[N:21]([O-])=[O:22].[Na+]>O>[N:21]([C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][C:4]=1[O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10130617HCID 10130617, compoundHCID 23668193Sodium Nitrite3×

Product 1

HCID 1810292,4-Pyrimidinediamine, 5-nitroso-6-(phenylmethoxy)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 16 g 2,4-diamino-6-benzyloxy-pyrimidine (7) in 250 mL of warm 30% acetic acid is added a solution of 7g sodium nitrite in 25 mL H2O. The sodium nitrite solution is held at 70°-80° C. and is added dropwise while being stirred continuously. The sodium nitrite solution is added until potassium-iodate starch paper shows a positive reaction. The violet-red precipitate is cooled, suctioned off and then recrystallized from ethanol or acetone to yield 8.

Workup

  1. customis held at 70°-80° C.
  2. additionis added dropwise
  3. customa positive reaction
  4. temperatureThe violet-red precipitate is cooled
  5. customrecrystallized from ethanol or acetone
  6. customto yield 8

Sources & evidence

ORD record
ord-49b5dd3038e74e94904b3800c18c25c5
Source dataset
uspto-grants-1996_06
Patent number
US05525711

Reaction notes

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