Diethyl (ethoxymethylene)malonate → Ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylate

HRID 714423노트

반응식

HRID 714423 반응식
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:10](=[NH:16])[NH:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[C:7]([F:9])[CH:8]=1.C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C.[O-]CC.[Na+]>C(O)C>[F:2][C:3]1[CH:4]=[C:5]([C:10]2[N:11]([CH2:12][CH2:13][O:14][CH3:15])[C:20](=[O:19])[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][N:16]=2)[CH:6]=[C:7]([F:9])[CH:8]=1

참가 물질

5

반응물 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 178495960HCID 178495960, 화합물2회

생성물 1

HCID 67955325Ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1 (i.e. the product from Example 9, Step B) (24.3 mmol) in ethanol (25 mL) was added diethyl ethoxymethylenemalonate (5.25 g, 24.3 mmol) followed by sodium ethoxide (21% soln) (9.1 mL, 24.3 mmol). The reaction mixture was heated and stirred at reflux for 24 h. The reaction mixture was cooled to room temperature concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (6.1 g).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with 50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-d89deebd92c740dc88e3c6509576e898
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187432B2

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