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

HRID 2374208Notes

Reaction equation

HRID 2374208 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-(pyridin-4-yl)-3-oxopropionate, 5.0 g (30.55 mmol) of 5,5-dimethyl-1,4,5,6-tetrahydro-2-pyrimidinamine monohydrochloride (prepared by analogy to the method described in 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 the method
  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-69a7b78c3b84478887d1baf6588e4969
Source dataset
uspto-grants-2008_12
Patent number
US07462621B2

Reaction notes

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