Phenethylamine → 1-(6-Phenethylamino-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

HRID 1785471Notes

Reaction equation

HRID 1785471 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH2:11][N:10]3[C:14](=[O:24])[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:17]=[C:9]23)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C.O.CCOC(C)=O>[CH2:31]([NH:39][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH2:11][N:10]3[C:14](=[O:24])[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:17]=[C:9]23)[CH:3]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 3

HCID 1001PhenethylamineHCID 11430Potassium CarbonateHCID 575931531-(6-Chloro-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

Product 1

HCID 114301641-(6-Phenethylamino-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 1-(6-chloro-pyrimidin-4-yl)-8-phenyl -1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one (0.158 mg, 0.47 mmol) and excess of K2CO3 in DMF (3 mL) was added phenethylamine (0.15 mL, 1.2 mmol). The overall reaction vessel was irradiated under microwave conditions at 150° C. for 10 min. After diluted with water and EtOAc, the organic layer was taken and the aqueous layer was extracted with EtOAc. The overall organic layers were washed with water, brine, and dried (Na2SO4). Filtration followed by evaporation gave the crude residue, which was washed with EtOAc/ether to provide the title compound as a light yellow solid. MS m/e 424 (M+H)+.

Workup

  1. customThe overall reaction vessel was irradiated under microwave conditions at 150° C. for 10 min
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe overall organic layers were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration
  6. customfollowed by evaporation
  7. customgave the crude residue, which
  8. washwas washed with EtOAc/ether

Sources & evidence

ORD record
ord-b2f3937799494752b8fbf7e0af1f7829
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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