2,6-Diamino-5-(2,2-diethoxyethyl)pyrimidin-4(1H)-one → HCID 135547466, compound

HRID 1638601Notes

Reaction equation

HRID 1638601 reaction equation
[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[CH2:5][C:6]1[C:11](=[O:12])[NH:10][C:9]([NH2:13])=[N:8][C:7]=1[NH2:14])[CH3:2]>C(OC(=O)C)(=O)C>[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[CH2:5][C:6]1[C:11](=[O:12])[NH:10][C:9]([NH:13][C:1](=[O:3])[CH3:2])=[N:8][C:7]=1[N:14]([C:4](=[O:15])[CH3:5])[C:11](=[O:12])[CH3:6])[CH3:2]

Participants

3

Reactant 1

HCID 1355690252,6-Diamino-5-(2,2-diethoxyethyl)pyrimidin-4(1H)-one

Product 1

HCID 135547466HCID 135547466, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Freshly distilled acetic anhydride (250 ml) was added to a solution of 2-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)acetaldehyde diethyl acetal (Chem. Ber., 1977, 110, 1462) (50.0 g, 0.206 mol). The solution was protected from moisture and heated on a steam bath with magnetic stirring for 5 days. The reaction was spin evaporated in vacuo with the addition of ethylene glycol monomethyl either under aspirator and finally mechanical pump vacuum. The residue was recrystallized from ether to yield 23.0 g (30% of theory) of 2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)acetaldehyde diethyl acetal, mp 128°-130°. The analytical sample was prepared by dissolving the sample in chloroform and washing the solution through Superfiltrol μ19 (Filtrol Corporation). The solution was spin evaporated in vacuo and the residue was recrystallized from ether/cyclohexanes, to give analytically pure material, mp 129°-130°.

Workup

  1. temperatureheated on a steam bath
  2. customevaporated in vacuo with the addition of ethylene glycol monomethyl either under aspirator and finally mechanical pump vacuum
  3. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-b0719299d3b84f938657f39c2688a7e3
Source dataset
uspto-grants-1989_11
Patent number
US04880812

Reaction notes

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