2-Methyl-2,3-dihydro-1-benzofuran-5-carboxylic acid → (-2Methylcoumaran-5-yl)-5-(4-octylphenyl)pyrimidine

HRID 3060노트

반응식

HRID 3060 반응식
Cl.[C:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([CH3:14])[CH2:8]2)(=[NH:4])[NH2:3].C([C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)O[CH:22]([CH3:27])[CH2:21]2)(O)=O.C[O-].[Na+]>CO>[CH3:14][CH:9]1[CH2:8][C:7]2[C:11](=[CH:12][CH:13]=[C:5]([C:2]3[N:3]=[CH:13][C:5]([C:26]4[CH:18]=[CH:19][C:20]([CH2:21][CH2:22][CH2:27][CH2:9][CH2:8][CH2:7][CH2:11][CH3:12])=[CH:24][CH:25]=4)=[CH:2][N:4]=3)[CH:6]=2)[O:10]1

참가 물질

5

반응물 3

HCID 6472552-Methyl-2,3-dihydro-1-benzofuran-5-carboxylic acidHCID 10942334Sodium MethoxideHCID 189343055-Amidino-2-methylcoumaran hydrochloride

생성물 1

HCID 18934307(-2Methylcoumaran-5-yl)-5-(4-octylphenyl)pyrimidine수율 58.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

0.40 g (1.88 mM) of 5-amidino-2-methylcoumaran hydrochloride (M5) as an intermediate product prepared in Example 1, 0.79 g (1.90 mM) of 3-dimethylamino-2-(4-octylphenyl)-N,N-dimethylpropene-(2)-ammonium perchlorate 0.41 g (7.59 mM) of sodium methylate and 15 ml of methanol were placed in a 50 ml-round bottomed flask and refluxed for 5 hours and 10 minutes under stirring. After the reaction, the reaction mixture was cooled on an ice-common salt bath to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water. The resultant crystal was dissolved in toluene and dried with mirabilite. After distilling-off of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent:toluene/ethyl acetate=100/1) and recrystallized from a mixture solvent of toluene and methanol to obtain 0.44 of 2 (-2methylcoumaran-5-yl)-5-(4-octylphenyl)pyrimidine (Ex. Comp. No. I-235) (Yield: 58.4%). The product showed the following phase transition temperatures (°C.). ##STR92##

후처리

  1. temperaturerefluxed for 5 hours and 10 minutes
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled on an ice-common salt bath
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. washby washing with water
  7. dissolutionThe resultant crystal was dissolved in toluene
  8. dry with materialdried with mirabilite
  9. distillationAfter distilling-off of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent:toluene/ethyl acetate=100/1)
  10. customrecrystallized from a mixture solvent of toluene and methanol

출처 및 근거

ORD 기록
ord-74043014bdd746ff9751b62ff8d91839
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733476

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