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

HRID 275921Notes

Reaction equation

HRID 275921 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.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:12][CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[N:22][C:23]=1[CH3:39]

Participants

5

Reactant 3

HCID 83551-NaphthalenemethanamineHCID 8471TriethylamineHCID 111853185,6-Dimethyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 699466925,6-Dimethyl-2-(1-naphthylmethyl)amino-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl) pyrimidine hydrochlorideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 1-naphthylmethylamine(0.38 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-dd57f181be2a42f4a9ef3b128438e688
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

Loading…