Water → 1-(4-chlorobutyl)-5-phenyl-2(1H)-pyrimidinone
Reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10](=[O:13])[NH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:22][CH2:23][CH2:24][CH2:25][Cl:26].O>ClCCl>[Cl:26][CH2:25][CH2:24][CH2:23][CH2:22][N:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[N:11][C:10]1=[O:13]Participants
Conditions
- Temperature
- 60 °C
Procedure
To a suspension of 5-phenyl-2(1H)-pyrimidinone (77 mg, 0.45 mmol, Aurora Screening Library or MDPI Product List or ref Helv. Chim. Acta, 10, 1927, 305//Collect. Czech. Chem. Commun., 61, 3, 1996, 458-477) in dry dichloromethane (4.0 ml), triethylamine (0.062 ml, 0.45 mmol) was added. The reaction mixture was stirred at room temperature for 30′, then 1-bromo-4-chlorobutane (0.052 ml, 0.44 mmol) was added and the reaction mixture was then heated at 40° C. for 24 hours and other 24 hours at 60° C. Water (22 ml) was added to the cold mixture and the organic layers were extracted with DCM (3×10 ml). The organic layers were combined and dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with DCM/methanol 96/4 to afford the title compound (60 mg, 51%).
Workup
- additionwas added
- additionwas added
- extractionthe organic layers were extracted with DCM (3×10 ml)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by column chromatography on silica gel eluting with DCM/methanol 96/4
Sources & evidence
- ORD record
- ord-04fc6779d4234310bff714f3b4f581f8
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222266B2
Reaction notes
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