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Potassium Carbonate → tert-Butyl 5-(benzyloxy)-2-{[1-(5-bromopyridin-2-yl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylate

HRID 1626810
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HRID 1626810 반응식
Cl.[CH2:2]([O:9][C:10]1[C:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:12][C:13]([CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:14][C:15]=1[CH3:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:32]1[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][N:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([O:9][C:10]1[C:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:12][C:13]([CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:32]3[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][N:33]=3)[CH2:20][CH2:19]2)=[N:14][C:15]=1[CH3:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 67156013tert-Butyl 5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidine-4-carboxylate hydrochloride

생성물 1

HCID 58257552tert-Butyl 5-(benzyloxy)-2-{[1-(5-bromopyridin-2-yl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylate수율 54.7%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

tert-Butyl 5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidine-4-carboxylate hydrochloride (6.5 g, 15 mmol), 2,5-dibromopyridine (5.3 g, 7.5 mmol) and potassium carbonate (6.2 g, 45 mmol) were suspended in N,N-dimethylformamide (150 mL), followed by stirring at 100° C. for 22 hours. The reaction solution was concentrated under reduced pressure, followed by addition of ethyl acetate, and subsequently the organic layer was washed with water. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (2.3 g, 4.1 mmol) as a colorless oil (yield 27%).

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionfollowed by addition of ethyl acetate
  3. washsubsequently the organic layer was washed with water
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  6. concentrationa fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1646245145b04f69b739554e3183614c
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785462B2

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