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Propylene Glycol → 5,6-Dimethyl-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-2-(4-fluoro-2-methoxyphenylamino)pyrimidine

HRID 275957
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인쇄 미리보기

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HRID 275957 반응식
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.[CH3:11][C:12]1[C:13]([N:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]2[CH3:30])=[N:14][C:15](Cl)=[N:16][C:17]=1[CH3:18].C(N(CC)CC)C.C(O)C(O)C>ClCCl>[CH3:11][C:12]1[C:13]([N:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]2[CH3:30])=[N:14][C:15]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=2[O:9][CH3:10])=[N:16][C:17]=1[CH3:18]
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참가 물질

6

반응물 4

HCID 1030Propylene GlycolHCID 8471TriethylamineHCID 111853185,6-Dimethyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidineHCID 135322284-Fluoro-2-methoxyaniline

생성물 1

HCID 183158005,6-Dimethyl-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-2-(4-fluoro-2-methoxyphenylamino)pyrimidine수율 75.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
140 °C

실험 절차

A reaction mixture of 4-fluoro-2-methoxy-aniline(0.155 g, 1.10 mmol), 5,6-dimethyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(0.24 lg, 0.84 mmol), triethylamine(0.15 ml, 1.1 mmol) and propyleneglycol (2 ml) was heated to 140° C. for 5 hours, cooled to a room temperature, diluted with dichloromethane(10 ml), and then washed with water. The separated organic layer was concentrated and the residual oil was purified by column chromatography(ethylacetate/N-hexane=1/1) to give 0.247 g of the titled compound. (Yield 75.2%)

후처리

  1. temperaturecooled to a room temperature
  2. washwashed with water
  3. concentrationThe separated organic layer was concentrated
  4. customthe residual oil was purified by column chromatography(ethylacetate/N-hexane=1/1)

출처 및 근거

ORD 기록
ord-ba7a292a6abe489faafeeb166958c34c
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06352993B1

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