Chloroacetaldehyde → 2-Amino-7-methyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

HRID 598182Notes

Reaction equation

HRID 598182 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[CH:5]=[C:4]([NH:9][CH3:10])[N:3]=1.Cl[CH2:12]C=O.[C:15](=[O:18])([O-])[O-].[K+].[K+]>CO>[NH2:1][C:2]1[NH:7][C:15](=[O:18])[C:5]2[CH:6]=[CH:12][N:9]([CH3:10])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 11430Potassium CarbonateHCID 178482274HCID 178482274, compound

Product 1

HCID 1354337232-Amino-7-methyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-oneYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-amino-6-(methylamino)pyrimidin-4-ol (40.5 g, 289 mmol) in methanol (300 ml) was added 40% aqueous chloroacetoaldehyde (51.6 ml, 318 mmol) and potassium carbonate (44.0 g, 318 mmol), and the mixture was refluxed for 1 hour. After cooling, the resulting crystals were collected by filtration and washed with water to give 19.4 g (41%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-b4cb5bd383654b8a8e20191683830e5e
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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