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

HRID 275937Notes

Reaction equation

HRID 275937 reaction equation
[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)[CH:27]2[CH3:36])[C:20]=1[CH3:37]>CN(C)C=O>[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)[CH:27]2[CH3:36])[C:20]=1[CH3:37]

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 8471TriethylamineHCID 183157576-Methoxymethyl-5-methyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183157386-Methoxymethyl-5-methyl-2-(2-methylphenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After o-toluidine(0.32 ml, 3.0 mmol) and triethylamine(0.63 ml, 4.5 mmol) were added to a solution of 6-methoxymethyl-5-methyl-2-chloro-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(0.96 g, 3 mmol) in dimethylformamide(5 ml), 250 mg of the titled compound was obtained in accordance with the same procedure as in Step 2 of Example 25.

Sources & evidence

ORD record
ord-56c3628d3ab245de9f5979f1bb6afa28
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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