Triethylamine → 1-methyl-2-[(2R)-2-methyl-4-(quinoline-2-carbonyl)-piperazin-1-yl]-1H-[4,4']bipyrimidinyl-6-one
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[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]1[CH3:21].C(N(CC)CC)C.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[C:39](Cl)=[O:40]>ClCCl>[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[N:15]1[CH2:20][CH2:19][N:18]([C:39]([C:30]2[CH:31]=[CH:32][C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:29]=2)=[O:40])[CH2:17][C@H:16]1[CH3:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4′]bipyrimidinyl-6-one (0.15 g, 0.52 mmol) and triethylamine (0.15 g, 1.48 mmol) in dichloromethane (2.5 ml) was added quinoline-2-carbonyl chloride (0.11 g, 0.57 mmol) at 0° C. and stirred for one hour at that temperature. The mixture was partitioned between water and dichloromethane, and the organic layer was washed with aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform/methanol=20/1) to afford 1-methyl-2-[(2R)-2-methyl-4-(quinoline-2-carbonyl)-piperazin-1-yl]-1H-[4,4′]bipyrimidinyl-6-one (0.18 g, 77%).
Workup
- customThe mixture was partitioned between water and dichloromethane
- washthe organic layer was washed with aqueous sodium hydrogen carbonate
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent; chloroform/methanol=20/1)
Sources & evidence
- ORD record
- ord-ac6c7d5a3974485b841978943c11b74a
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569294B2
Reaction notes
Loading…