Tributylamine → 2-(2-n-Propoxyphenyl)-8-(1-Hepten-1-yl)Quinazolin-4(3H)-One

HRID 635196

반응식

HRID 635196 반응식
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:20][C:19](=[O:21])[C:18]2[C:13](=[C:14](I)[CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH2:2][CH3:3].C(N(CCCC)CCCC)CCC.[CH2:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:20][C:19](=[O:21])[C:18]2[C:13](=[C:14]([CH:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH2:2][CH3:3]

참가 물질

8

반응물 4

HCID 7622TributylamineHCID 116101-HepteneHCID 80271Tri-o-tolylphosphineHCID 1355493722-(2-n-Propoxyphenyl)-8-Iodoquinazolin-4(3H)-One

생성물 1

HCID 1361324752-(2-n-Propoxyphenyl)-8-(1-Hepten-1-yl)Quinazolin-4(3H)-One

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

5 g (12.31 mmoles) of the compound from Example III, 3.7 ml (15.4 mmoles) of tributylamine, 6.6 ml (46.2 mmoles) of 1-heptene, 375 mg of tri-o-tolylphosphine (1.23 mmoles), and 138 mg of palladium(II) acetate (0.6 mmole) are stirred in 50 ml of dry DMF for 2.5 h at 100° C. The mixture is cooled to room temperature, 50 ml of ethyl acetate is added, and the mixture is washed 3 times with 50-ml portions of H2O. After drying over MgSO4, the organic phase is evaporated under vacuum, and the residue is chromatographed on silica gel with toluene/ethyl acetate 95:5 as eluant. The fractions containing the product are combined and the solvent is evaporated under vacuum. The initially oily residue is crystallized by stirring with 35 ml petroleum ether.

후처리

  1. washthe mixture is washed 3 times with 50-ml portions of H2O
  2. dry with materialAfter drying over MgSO4
  3. customthe organic phase is evaporated under vacuum
  4. customthe residue is chromatographed on silica gel with toluene/ethyl acetate 95:5 as eluant
  5. additionThe fractions containing the product
  6. customthe solvent is evaporated under vacuum
  7. customThe initially oily residue is crystallized

출처 및 근거

ORD 기록
ord-ba80d6ece68343afbfd689bba07309fb
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187779B1

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