Pentafluoropropylamidine → HCID 86660090, 화합물

HRID 1843106노트

반응식

HRID 1843106 반응식
[F:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[C:3](=[NH:5])[NH2:4].C(O/[CH:14]=[C:15](/[C:21](=O)[CH:22]([F:24])[F:23])\[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.C[O-].[Na+]>C(O)C>[F:23][CH:22]([F:24])[C:21]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:4]=[C:3]([C:2]([F:10])([F:1])[C:6]([F:9])([F:8])[F:7])[N:5]=1

참가 물질

5

반응물 3

HCID 3681554PentafluoropropylamidineHCID 10942334Sodium MethoxideHCID 44185486HCID 44185486, 화합물

생성물 1

HCID 86660090HCID 86660090, 화합물수율 39.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1.620 g (10 mmol) of 2,2,3,3,3-pentafluoropropanimidamide (commercially available) and 2.222 g (10 mmol) of ethyl (2Z)-2-(ethoxymethylidene)-4,4-difluoro-3-oxobutanoate (for preparation see WO 2005/123690) in 10 ml of absolute ethanol is stirred under reflux for 4 days after adding 0.680 g (10 mmol) of sodium methylate. The mixture is then concentrated by evaporation in vacuo and the residue is taken up in 10 ml of water and extracted twice with 10 ml of ethyl acetate. The organic phases are washed successively with 5 ml of water and 5 ml of saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated by evaporation in vacuo. Chromatographic purification with a mixture of cyclohexane and ethyl acetate gives 1.264 g (3.95 mM, 39.5% of theory) of ethyl 4-(difluoromethyl)-2-(pentafluoroethyl)pyrimidine-5-carboxylate as a white solid.

후처리

  1. temperatureunder reflux for 4 days
  2. concentrationThe mixture is then concentrated by evaporation in vacuo
  3. extractionextracted twice with 10 ml of ethyl acetate
  4. washThe organic phases are washed successively with 5 ml of water and 5 ml of saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation in vacuo
  8. customChromatographic purification
  9. additionwith a mixture of cyclohexane and ethyl acetate

출처 및 근거

ORD 기록
ord-a4d62c80572c4a6b8567c263623cbeeb
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946234B2

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