2-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine → 4-(1,2,3,4-Tetrahydroquinolin-1-yl)-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}pyrimidine

HRID 2083896Notes

Reaction equation

HRID 2083896 reaction equation
[OH:1][CH:2]([CH2:27][N:28]([CH3:30])[CH3:29])[CH2:3][O:4][C:5]1[CH:26]=[CH:25][C:8]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)[CH:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1.Cl[C:32]1N=C(N2C3C(=CC=CC=3)CCC2)C=CN=1>>[N:16]1([C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:9][C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:27][N:28]([CH3:29])[CH3:30])=[CH:26][CH:25]=3)[N:15]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:32][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 227319232-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidineHCID 22731924HCID 22731924, compound

Product 1

HCID 227319254-(1,2,3,4-Tetrahydroquinolin-1-yl)-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}pyrimidine

Procedure

Using an analogous method to that described in Example 1, but starting from 4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]aniline hydrochloride (Method 1) and 2-chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine (Method 8), the product was obtained. NMR: 1.8-2.0 (m, 2H), 2.19 (s, 6H), 2.2-2.3 (m, 1H), 2.3-2.45 (m, 1H), 2.7-2.8 (m, 2H), 3.7-3.9 (m, 5H), 5.7 (m, 1H), 6.35 (m, 2H), 6.8 (m, 2H), 7.0-7.05 (m, 1H), 7.1-7.2 (m, 2H), 7.35-7.4 (m, 1H), 7.5-7.6 (m, 2H), 7.9-8.0 (m, 2H), 8.95 (s, 1H); MS (MH+): 420.5.

Workup

  1. customthe product was obtained

Sources & evidence

ORD record
ord-02ef5b27d3d34f37947ebbe685e92fb9
Source dataset
uspto-grants-2004_04
Patent number
US06716831B1

Reaction notes

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