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Water → Methyl 7-cyclopentyl-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

HRID 79141
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HRID 79141 반응식
[H-].[Na+].[CH:3]1([N:8]([C:14]2[C:19]([CH:20]=O)=[CH:18][N:17]=[C:16]([S:22][CH3:23])[N:15]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4]1.O>CCCCCC.C1C=CC=CC=1>[CH:3]1([N:8]2[C:14]3[N:15]=[C:16]([S:22][CH3:23])[N:17]=[CH:18][C:19]=3[CH:20]=[C:9]2[C:10]([O:12][CH3:13])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4]1
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참가 물질

6

반응물 3

HCID 962WaterHCID 24758Sodium hydrideHCID 58299719Methyl 2-(cyclopentyl(5-formyl-2-(methylthio)pyrimidin-4-yl)amino)acetate

생성물 1

HCID 58299712Methyl 7-cyclopentyl-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate수율 34.8%

시약·촉매·용매 2

HCID 241Benzene용매
HCID 8058
Hexane
용매

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온도
70 °C

실험 절차

Sodium hydride (3.85 g, 167 mmol) (freshly washed with hexane) was added to a solution of compound 226 (12.95 g, 41.9 mmol) in benzene (150 mL). The reaction was stirred at 70° C. After 1 h, the reaction contents were poured into water (300 mL) and extracted with ethyl acetate (2×100 mL). The combined organics were washed with brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography (gradient elution 0 to 50% ethyl acetate in hexanes) afforded compound 227 (4.24 g, 34.8% yield).

후처리

  1. customthe reaction contents
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography (gradient elution 0 to 50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-934a3dcf4f314798a4474657b46590f3
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841312B2

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