Phenethylamine → 5,6-Dimethyl-2-phenylethylamino-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

HRID 275920Notes

Reaction equation

HRID 275920 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:17][C:18]1[N:23]=[C:22]([N:24]2[CH2:33][CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]2[CH3:34])[C:21]([CH3:35])=[C:20]([CH3:36])[N:19]=1>CN(C)C=O>[ClH:17].[CH3:35][C:21]1[C:22]([N:24]2[CH2:33][CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]2[CH3:34])=[N:23][C:18]([NH:9][CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[N:19][C:20]=1[CH3:36]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 111853185,6-Dimethyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183158395,6-Dimethyl-2-phenylethylamino-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 2-phenethylamine(0.33 ml, 2.61 mmol) and triethylamine(0.36 ml, 2.59 mmol) were added to a solution of 2-chloro-5,6-dimethyl-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(0.5 g, 1.74 mmol) in dimethylformamide, 500 mg of the titled compound was obtained in accordance with the same procedure as in Example 1.

Sources & evidence

ORD record
ord-6fc08ba3910941b9aac4a9fa3e19c659
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

Loading…