Aniline → 6-Methoxymethyl-5-methyl-2-phenylamino-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

HRID 275938Notes

Reaction equation

HRID 275938 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:15][O:16][CH2:17][C:18]1[N:23]=[C:22]([Cl:24])[N:21]=[C:20]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]2[CH3:35])[C:19]=1[CH3:36]>CN(C)C=O>[ClH:24].[CH3:15][O:16][CH2:17][C:18]1[N:23]=[C:22]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:21]=[C:20]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]2[CH3:35])[C:19]=1[CH3:36]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 183157576-Methoxymethyl-5-methyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183157986-Methoxymethyl-5-methyl-2-phenylamino-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After aniline (2.41 ml, 26.4 mmol) and triethylamine(3.68 ml, 26.4 mmol) were added to a solution of 6-methoxymethyl-5-methyl-2-chloro-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(7 g, 22 mmol) in dimethylformamide (20 ml), 4.1 g of the titled compound was obtained in accordance with the same procedure as in Step 2 of Example 25.

Sources & evidence

ORD record
ord-58827b100a764d5ba307ccf3be529e10
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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