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

HRID 275945Notes

Reaction equation

HRID 275945 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][C:17]1[C:18]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[O:35][CH3:36])[CH:26]2[CH3:37])=[N:19][C:20]([Cl:24])=[N:21][C:22]=1[CH3:23]>CN(C)C=O>[ClH:24].[CH3:16][C:17]1[C:18]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[O:35][CH3:36])[CH:26]2[CH3:37])=[N:19][C:20]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)=[N:21][C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 183158305,6-Dimethyl-2-chloro-4-(5-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183157695,6-Dimethyl-2-(4-fluorophenylarnino)-4-(5-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 4-fluoroaniline(0.32 ml, 3.3 mmol) and triethylamine(0.46 ml, 3.3 mmol) were added to a solution of 5,6-dimethyl-2-chloro-4-(5-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(0.7 g, 2.2 mmol) in dimethylformamide (5 ml), 0.55 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-645014b4ed314461996d3dd5cb04e7f7
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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