Triethylamine → 5,6-Dimethyl-2-(3-trifluoromethylphenylmethyl)amino-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

HRID 275922Notes

Reaction equation

HRID 275922 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].C(N(CC)CC)C.[Cl:20][C:21]1[N:26]=[C:25]([N:27]2[CH2:36][CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]2[CH3:37])[C:24]([CH3:38])=[C:23]([CH3:39])[N:22]=1>CN(C)C=O>[ClH:20].[CH3:38][C:24]1[C:25]([N:27]2[CH2:36][CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]2[CH3:37])=[N:26][C:21]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=2)=[N:22][C:23]=1[CH3:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 759623-(Trifluoromethyl)benzylamineHCID 111853185,6-Dimethyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183157835,6-Dimethyl-2-(3-trifluoromethylphenylmethyl)amino-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 3-trifluoromethylbenzylamine(0.30 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, 630 mg of the titled compound was obtained in accordance with the same procedure as in Example 1.

Sources & evidence

ORD record
ord-c6e4741c539243bcb01ccc232985ee5b
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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