Potassium Carbonate → 1-methyl-2-{(2R)-2-methyl-4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-piperazin-1-yl}-1H-[4,4']bipyrimidinyl-6-one

HRID 1045698ノート

反応式

HRID 1045698 の反応式
[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(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:40]=[C:39]([CH3:41])[O:38][N:37]=2)=[CH:32][CH:31]=1>CN(C)C=O>[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]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]3[N:40]=[C:39]([CH3:41])[O:38][N:37]=3)=[CH:34][CH:35]=2)[CH2:17][C@H:16]1[CH3:21]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 71645903-(4-(Bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazoleHCID 250045961-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4']bipyrimidinyl-6-one

生成物 1

HCID 578698601-methyl-2-{(2R)-2-methyl-4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-piperazin-1-yl}-1H-[4,4']bipyrimidinyl-6-one収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 potassium carbonate (0.22 g, 1.59 mmol) in N,N-dimethylformamide (1.5 ml) was added 3-[4-(bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole (0.14 g, 0.55 mmol) at room temperature and the mixture was stirred for 4 hours. The mixture was partitioned between water and dichloromethane, and the organic layer was washed with water, brine, and dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford 1-methyl-2-{(2R)-2-methyl-4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-piperazin-1-yl}-1H-[4,4′]bipyrimidinyl-6-one (0.15 g, 63%).

後処理

  1. customThe mixture was partitioned between water and dichloromethane
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

出典と根拠

ORDレコード
ord-ad98122cfc56480bb8732737608a1a3c
出典データセット
uspto-grants-2013_10
特許番号
US08569294B2

反応ノート

読み込み中…