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

HRID 275951Notes

Reaction equation

HRID 275951 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][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]=[C:31]([O:36][CH3:37])[CH:32]=3)[CH:27]2[CH3:38])[C:20]=1[CH3:39]>CN(C)C=O>[ClH:25].[CH3:16][O:17][CH2:18][C:19]1[N:24]=[C:23]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)[N:22]=[C:21]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:36][CH3:37])[CH:32]=3)[CH:27]2[CH3:38])[C:20]=1[CH3:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 183156576-Methoxymethyl-5-methyl-2-chloro-4-(1-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183157626-Methoxymethyl-5-methyl-2-(4-fluorophenylamino)-4-(1-methyl-6-methoxy-1,2, 3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideYield 53.4%

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 6-methoxymethyl-5-methyl-2-chloro-4-(1-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine (1.0 g, 2.3 mmol) in dimethylformamide(5 ml), 0.56 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-3012cdddb7f24e8bb5ac54b54e7de7b7
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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