Potassium Carbonate → 8-Phenyl-2-(4-pyridinyl)-6,7,8,9-tetrahydro-4H-pyrimido[1.2-a]pyrimidin-4-one

HRID 1296428Notes

Reaction equation

HRID 1296428 reaction equation
Cl.[C:2]1([CH:8]2[NH:13][C:12]([NH2:14])=[N:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH2:22][C:23](OCC)=[O:24])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:2]1([CH:8]2[CH2:9][CH2:10][N:11]3[C:23](=[O:24])[CH:22]=[C:21]([C:18]4[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=4)[N:14]=[C:12]3[NH:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 230261524-Phenyl-1,4,5,6-tetrahydropyrimidin-2-amine hydrochloride

Product 1

HCID 1357802668-Phenyl-2-(4-pyridinyl)-6,7,8,9-tetrahydro-4H-pyrimido[1.2-a]pyrimidin-4-oneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A suspension containing 4 g (16.12 mmoles) of 6-phenyl-1,4,5,6-tetrahydro-2-pyrimidinamine hydrochloride (1:2), 3.11 g (16.12 mmoles) of ethyl 3-(pyridin-4-yl)-3-oxopropionate, 6.68 g (48.36 mmoles) of anhydrous potassium carbonate in 50 ml of ethanol were refluxed for 18 h. The cooled solution was evaporated and the residue was treated with water and allowed to stir at 0° C. during 2 h. The precipitate which formed was recovered by filtration and dried at 90° C. during 18 h. 4.80 g (98%) of product was thus obtained.

Workup

  1. temperaturewere refluxed for 18 h
  2. customThe cooled solution was evaporated
  3. additionthe residue was treated with water
  4. customThe precipitate which formed
  5. filtrationwas recovered by filtration
  6. customdried at 90° C. during 18 h

Sources & evidence

ORD record
ord-c99bf11c38b94749a42eb2e5176e3179
Source dataset
uspto-grants-2007_07
Patent number
US07247638B2

Reaction notes

Loading…