Potassium Carbonate → 7,7-Dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

HRID 2375322Notes

Reaction equation

HRID 2375322 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9]([O:11]CC)=O)=[CH:3][CH:2]=1.Cl.[CH3:16][C:17]1([CH3:24])[CH2:22][NH:21][C:20]([NH2:23])=[N:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.ClCCl>[CH3:16][C:17]1([CH3:24])[CH2:22][N:21]2[C:9](=[O:11])[CH:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[N:23]=[C:20]2[NH:19][CH2:18]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 234662455,5-Dimethyl-1,4,5,6-tetrahydropyrimidin-2-amine hydrochloride

Product 1

HCID 1357386167,7-Dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-oneYield 80.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.9 g (30.55 mmol) of ethyl 3-(4-pyridyl)-3-oxopropionate, 5.0 g (30.55 mmol) of 5,5-dimethyl-1,4,5,6-tetrahydro-2-pyrimidinamine monohydrochloride (prepared by analogy to U.S. Pat. No. 4,262,122) and 6.33 g (45.82 mmol) of potassium carbonate in 60 ml of ethanol was heated at reflux temperature during 12 h. The cooled suspension was filtered and the solvent removed by evaporation. The residue obtained was dissolved in dichloromethane and washed with water. The organic phase was dried and evaporated to give 6.30 g (80%) of product as a beige solid. Mp.: 152-154° C.

Workup

  1. customprepared by analogy to U.S
  2. temperatureat reflux temperature during 12 h
  3. filtrationThe cooled suspension was filtered
  4. customthe solvent removed by evaporation
  5. customThe residue obtained
  6. washwashed with water
  7. customThe organic phase was dried
  8. customevaporated

Sources & evidence

ORD record
ord-c4d1ef3ebb234d3c85dca234be12a751
Source dataset
uspto-grants-2008_12
Patent number
US07465737B2

Reaction notes

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