O-Toluidine → 6-Methoxymethyl-5-methyl-2-(2-methylphenylamino)-4-(1,2,3,4-tetrahydro isoquinolin-2-yl)pyrimidine hydrochloride

HRID 275931

반응식

HRID 275931 반응식
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:16][O:17][CH2:18][C:19]1[N:24]=[C:23]([Cl:25])[N:22]=[C:21]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]2)[C:20]=1[CH3:36]>CN(C)C=O.ClCCl>[ClH:25].[CH3:16][O:17][CH2:18][C:19]1[N:24]=[C:23]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:8])[N:22]=[C:21]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]2)[C:20]=1[CH3:36]

참가 물질

6

반응물 3

HCID 7242O-ToluidineHCID 8471TriethylamineHCID 183157876-Methoxymethyl-5-methyl-2-chloro-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

생성물 1

HCID 183158106-Methoxymethyl-5-methyl-2-(2-methylphenylamino)-4-(1,2,3,4-tetrahydro isoquinolin-2-yl)pyrimidine hydrochloride수율 32.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
130 °C

실험 절차

o-Toluidine(0.48 ml, 4.5 mmol) and triethylamine were added to a solution of 6-methoxymethyl-5-methyl-2-chloro-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine (0.9 g, 3 mmol) in dimethylformamide(5 ml) and stirred for 5 hours at 130° C. The reaction mixture was cooled to a room temperature, diluted with dichloromethane, and washed with aqueous sodium hydroxide and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the residual oil was purified by column chromatography. The purified compound was dissolved in ethyl ether. Ethyl ether saturated with hydrochloric acid was added to a mixture solution. The resulting solid was filtered and dried to give 400 mg of the titled compound.

후처리

  1. temperatureThe reaction mixture was cooled to a room temperature
  2. washwashed with aqueous sodium hydroxide and water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe residual oil was purified by column chromatography
  6. dissolutionThe purified compound was dissolved in ethyl ether
  7. additionEthyl ether saturated with hydrochloric acid was added to a mixture solution
  8. filtrationThe resulting solid was filtered
  9. customdried

출처 및 근거

ORD 기록
ord-305f6026270e46898cae1cd4b3176bc2
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352993B1

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