4-Fluoro-2-methylaniline → 6-Ethyl-2-(2-methyl-4-fluorophenylamino)-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

HRID 1289542Notes

Reaction equation

HRID 1289542 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10]([C:12]1[N:17]=[C:16]([Cl:18])[N:15]=[C:14]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)[CH:13]=1)[CH3:11]>CN(C)C=O>[ClH:18].[CH2:10]([C:12]1[N:17]=[C:16]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=2[CH3:1])[N:15]=[C:14]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)[CH:13]=1)[CH3:11]

Participants

4

Reactant 2

HCID 679824-Fluoro-2-methylanilineHCID 189217966-Ethyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2-chloropyrimidine

Product 1

HCID 189217256-Ethyl-2-(2-methyl-4-fluorophenylamino)-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 2-methyl-4-fluoroaniline(0.57 ml, 5.13 mmol) was added to a mixture solution of 6-ethyl-4-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2-chloropyrimidine(0.7 g, 2.56 mmol) and dimethylformamide(5 ml), 0.55 g of the titled compound was obtained in accordance with the same procedure as in Step 2 of Example 1.

Sources & evidence

ORD record
ord-b630687558814769b6bb3712d25ff71b
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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