2-Methoxyethylamine → 5,6-Dimethyl-2-(2-methoxyethylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl) pyrimidine

HRID 275919Notes

Reaction equation

HRID 275919 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.Cl[C:14]1[N:19]=[C:18]([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])[C:17]([CH3:31])=[C:16]([CH3:32])[N:15]=1>CN(C)C=O>[CH3:31][C:17]1[C:18]([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:19][C:14]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[N:15][C:16]=1[CH3:32]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 111853185,6-Dimethyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183158065,6-Dimethyl-2-(2-methoxyethylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl) pyrimidineYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 2-methoxyethylamine(0.23 ml, 2.7 mmol) and triethylamine(0.38 ml, 2.7 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, 320 mg of the titled compound was obtained in accordance with the same procedure as in Example 1.

Sources & evidence

ORD record
ord-37b86e61141e42c29cd0234632c86256
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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