Water → 2-Chloro-5-(cyclopentyloxy)pyrimidine

HRID 250047

반응식

HRID 250047 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.Cl[CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70252ChlorocyclopentaneHCID 145957002-Chloro-5-pyrimidinol

생성물 1

HCID 574765592-Chloro-5-(cyclopentyloxy)pyrimidine수율 54.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

A mixture of 2-chloropyrimidin-5-ol (1 g, 7.66 mmol), chlorocyclopentane (2.39 mL, 22.98 mmol) and potassium carbonate (3.18 g, 22.98 mmol) in N,N-dimethylformamide were heated at 65° C. for 16 h at ambient temperature. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (0-25% ethyl acetate/hexanes) to afford 2-chloro-5-(cyclopentyloxy)pyrimidine (831 mg, 4.18 mmol, 54.6% yield) as a white solid. MS (LC/MS) R.T.=2.32; [M+H]+=199.23.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (0-25% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-d196ad7835c64c4ea90be1cb5b70642f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863291B2

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