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 1045698노트

반응식

HRID 1045698 반응식
[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]

참가 물질

5

반응물 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

생성물 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-one수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ad98122cfc56480bb8732737608a1a3c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569294B2

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