3,5-Dimethylaniline → 2-(3,5-dimethylphenylamino)-3H-pyrimidin-4-one
Reaction equation
CS[C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[CH3:10][C:11]1[CH:12]=[C:13]([CH:15]=[C:16]([CH3:18])[CH:17]=1)[NH2:14]>C(OCCOCCOCC)C>[CH3:10][C:11]1[CH:12]=[C:13]([NH:14][C:3]2[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=2)[CH:15]=[C:16]([CH3:18])[CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
2-(Methylthio)pyrimidin-4(3H)-one (4-1, 2.00 g, 14.1 mmol) and 3,5-dimethylaniline (2.10 ml, 16.9 mmol) were stirred in 14 ml of 2-ethoxyethyl ether and the resulting solution was heated to 170° C. After 3 days the reaction was concentrated in vacuo. The residue was diluted with 95:5 DCM/MeOH. The solid, which did not dissolve, was filtered to afford a sample of pure 2-(3,5-dimethylphenylamino)-3H-pyrimidin-4-one. The filtrate was concentrated in vacuo and the residue was triturated with ether. The mixture was filtered and the solid was washed with ether. The solid sample was combined with the previous precipitate to afford 2-(3,5-dimethyl-phenylamino)-3H-pyrimidin-4-one.
Workup
- concentrationAfter 3 days the reaction was concentrated in vacuo
- additionThe residue was diluted with 95:5 DCM/MeOH
- dissolutionThe solid, which did not dissolve
- filtrationwas filtered
Sources & evidence
- ORD record
- ord-71a5f3ee979c4b2bbffb1ed034f62251
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06958340B2
Reaction notes
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