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

HRID 275936Notes

Reaction equation

HRID 275936 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[CH3:17][O:18][CH2:19][C:20]1[N:25]=[C:24]([Cl:26])[N:23]=[C:22]([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:21]=1[CH3:38]>CN(C)C=O>[ClH:26].[CH3:17][O:18][CH2:19][C:20]1[N:25]=[C:24]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=2[CH3:1])[N:23]=[C:22]([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:21]=1[CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 679824-Fluoro-2-methylanilineHCID 183157576-Methoxymethyl-5-methyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183157906-Methoxymethyl-5-methyl-2-(2-methyl-4-fluorophenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 2-methyl-4-fluoroaniline(0.62 ml, 4.5 mmol) and triethylamine (0.63 ml, 4.5 mmol) were added to a solution of 6-methoxymethyl-5-methyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(0.96 g, 3 mmol) in dimethylformamide(5 ml), 600 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-4b81df0122b14faab8e36eee61055e19
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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