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

HRID 275931

反応式

HRID 275931 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-305f6026270e46898cae1cd4b3176bc2
出典データセット
uspto-grants-2002_03
特許番号
US06352993B1

関連ノート

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