Reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[CH3:22][N:23]([CH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)[CH3:24].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:24][N:23]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([N:19]2[CH2:20][CH2:21][CH:16]([O:15][C:3]3[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[C:5]([C:9]4[CH:14]=[CH:13][N:12]=[CH:11][N:10]=4)[N:4]=3)[CH2:17][CH2:18]2)=[O:31])=[CH:33][CH:34]=1)[CH3:22]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 1-methyl-2-(piperidin-4-yloxy)-1H-[4,4′]bipyrimidinyl-6-one (290 mg, 1.0 mmol), 4-dimethylaminomethyl benzoic acid (180 mg, 1.0 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (380 mg, 2.0 mmol) and 1-hydroxybenzotriazole monohydrate (310 mg, 2.0 mmol) in N,N-dimethylformamide (10 ml) was added N,N-diisopropylethylamine (130 mg, 1.0 mmol) at room temperature. The mixture was stirred at room temperature for 3 hours. The mixture was partitioned between water and dichloromethane. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=15/85) to afford 2-[1-(4-dimethylaminomethyl-benzoyl)piperidin-4-yloxy]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one as a colorless solid (66 mg, 0.15 mmol, 15%).
Workup
- customThe mixture was partitioned between water and dichloromethane
- washThe organic layer was washed with water (three times)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=15/85)
Sources & evidence
- ORD record
- ord-819aea120ff84d509a8ebc70598cd722
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006232B2
Linked notes
Loading…