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N,N-Diethylaniline → 3-(2-Heptyloxycarbonyl)-2,6-dimethyl-5-(3-methyl-2-butenyloxycarbonyl)-4-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidine

HRID 2119166
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HRID 2119166 반응식
C(N(CC)CC)C.[CH3:8][CH:9]1[N:14]=[C:13]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[C:12]([C:27]([O:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])=[O:28])=[C:11]([CH3:35])[NH:10]1.C(N(CC)C1C=CC=CC=1)C.C(O)C#CCCCC.[Cl:55][C:56]([O:58][CH:59]([CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH3:60])=[O:57]>O1CCCC1.ClC(OC(Cl)(Cl)Cl)=O>[Cl:55][C:56]([O:58][CH:59]([CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH3:60])=[O:57].[CH3:60][CH:59]([O:58][C:56]([N:14]1[CH:13]([C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)[C:12]([C:27]([O:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])=[O:28])=[C:11]([CH3:35])[N:10]=[C:9]1[CH3:8])=[O:57])[CH2:61][CH2:62][CH2:63][CH2:64][CH3:65]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 7061N,N-DiethylanilineHCID 8471TriethylamineHCID 5351112-Heptyn-1-olHCID 201911132,6-Dimethyl-5-(3-methyl-2-butenyloxycarbonyl)-4-(3,4,5-trimethoxyphenyl)-dihydropyrimidineHCID 214878432-Heptyl chloroformate

생성물 2

HCID 214878432-Heptyl chloroformate
HCID 54016747
3-(2-Heptyloxycarbonyl)-2,6-dimethyl-5-(3-methyl-2-butenyloxycarbonyl)-4-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrimidine
수율 69%

시약·촉매·용매 2

HCID 10426Diphosgene촉매HCID 8028Tetrahydrofuran용매4회

실험 절차

0.5 ml of Triethylamine was added to a solution of 200 mg of 2,6-dimethyl-5-(3-methyl-2-butenyloxycarbonyl)-4-(3,4,5-trimethoxyphenyl)-dihydropyrimidine in 5 ml of tetrahydrofuran (THF) and 2-heptyl chloroformate dissolved in 6 ml of THF was added dropwise. The 2-heptyl chloroformate was prepared by adding 0.25 ml of N,N-diethylaniline dissolved in 2 ml of THF to a solution of 0.15 g of 2-heptyn-1-ol and 0.1 mg of trichloromethyl chloroformate in 4 ml of THF in a separate reaction vessel. After stirring at room temperature for 1 hr, the reaction mixture was concentrated under reduced pressure. The residue was purified on silica gel by column chromatography (silica gel 20 g, eluant:benzene/ethyl acetate 9:1) to obtain 187 mg (69% yield) of title product.

후처리

  1. additionwas added dropwise
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified on silica gel by column chromatography (silica gel 20 g, eluant:benzene/ethyl acetate 9:1)

출처 및 근거

ORD 기록
ord-c37654dacc504cea930d348b925596f8
출처 데이터셋
uspto-grants-1987_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04683234

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