5-Nitroso-2,4,6-pyrimidinetriamine → 2,4,7-Triamino-6-(p-acetoxyphenyl)-pteridine

HRID 1156267Notes

Reaction equation

HRID 1156267 reaction equation
[Na].[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([N:10]=O)=[C:5]([NH2:12])[N:4]=1.[C:13]([O:16][C:17]1[CH:25]=[CH:24][C:20]([CH2:21][C:22]#[N:23])=[CH:19][CH:18]=1)(=[O:15])[CH3:14]>C(OCCO)C>[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]2[C:5](=[N:12][C:22]([NH2:23])=[C:21]([C:20]3[CH:19]=[CH:18][C:17]([O:16][C:13](=[O:15])[CH3:14])=[CH:25][CH:24]=3)[N:10]=2)[N:4]=1

Participants

5

Reactant 3

HCID 705045-Nitroso-2,4,6-pyrimidinetriamineHCID 5360545SodiumHCID 15628731p-Acetoxybenzylcyanide

Product 1

HCID 205357152,4,7-Triamino-6-(p-acetoxyphenyl)-pteridine

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

410 mg metallic sodium were dissolved while stirring in 100 ml of 2-ethoxy ethanol. Thereafter, 1100 mg 2,4,6-Triaminonitrosopyrimidine are added while stirring together with 1140 mg p-acetoxybenzylcyanide and the mixture is heated while stirring up to the boiling point. The color of the mixture changed from violet to brown. After two hours boiling under reflux, the heat is turned off and the reaction mixture is allowed to cool. Thereafter, 70 to 80% of the 2-ethoxyethanol is distilled under the vacuum of the water system, and the residue is taken up in 500 mls of water. After four-fold extraction with ether the pH is adjusted to pH 5 with 2 N hydrochloric acid. The precipitate is filtered, it is washed with a small amount of ice-cold acetone and recrystallized from 10% acetic acid. Further purification can be carried out over a silica gel column. The title compound obtained melts at 319°-321° C. (carbonization).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. distillationThereafter, 70 to 80% of the 2-ethoxyethanol is distilled under the vacuum of the water system
  5. extractionAfter four-fold extraction with ether the pH
  6. filtrationThe precipitate is filtered
  7. washit is washed with a small amount of ice-cold acetone
  8. customrecrystallized from 10% acetic acid
  9. customFurther purification

Sources & evidence

ORD record
ord-55bfc357f67043e7bcb11c0e856a2e0e
Source dataset
uspto-grants-1982_06
Patent number
US04335119

Reaction notes

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