4-(4-Methylpiperazin-1-yl)aniline → 6-Bromo-8-ethyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 387216Notes

Reaction equation

HRID 387216 reaction equation
[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH2:16][CH3:17])[C:5]2[N:6]=[C:7](S(C)=O)[N:8]=[CH:9][C:4]=2[CH:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>>[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH2:16][CH3:17])[C:5]2[N:6]=[C:7]([NH:29][C:28]3[CH:27]=[CH:26][C:25]([N:22]4[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]4)=[CH:31][CH:30]=3)[N:8]=[CH:9][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 671196106-Bromo-8-ethyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 667604546-Bromo-8-ethyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-8H-pyrido[2,3-d]pyrimidin-7-oneYield 40.5%

Procedure

6-Bromo-8-ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (4, 600 mg, 1.90 mmol) and 4-(4-methylpiperazino)aniline (363 mg, 1.90 mmol) were stirred at 120° C. for 3 h. The reaction mixture was purified by column chromatography using dichloromethane:methanol (100:3→100:5) to give the title compound (340 mg, 0.77 mmol, 40%) as a yellow solid. ESMS m/z 443 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.47 (s, 1H) 7.92 (s, 1H) 7.51 (d, J=8.8 Hz, 2H) 7.24 (br. s., 1H) 6.96 (d, J=8.8 Hz, 2H) 4.48 (q, J=7.0 Hz, 2H) 3.13-3.29 (m, 4H) 2.53-2.64 (m, 4H) 2.36 (s, 3H) 1.35 (t, J=7.0 Hz, 3H).

Workup

  1. customThe reaction mixture was purified by column chromatography

Sources & evidence

ORD record
ord-3d3ee01b5907479daa49ccd078d90bcf
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

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