4-(4-Methylpiperazin-1-yl)aniline → 8-(2-cyclopropylbenzyl)-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1188718Notes

Reaction equation

HRID 1188718 reaction equation
[CH:1]1([C:4]2[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=2[CH2:6][N:7]2[C:12]3[N:13]=[C:14](S(C)=O)[N:15]=[CH:16][C:11]=3[CH:10]=[CH:9][C:8]2=[O:20])[CH2:3][CH2:2]1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1>>[CH:1]1([C:4]2[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=2[CH2:6][N:7]2[C:12]3[N:13]=[C:14]([NH:36][C:35]4[CH:34]=[CH:33][C:32]([N:29]5[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]5)=[CH:38][CH:37]=4)[N:15]=[CH:16][C:11]=3[CH:10]=[CH:9][C:8]2=[O:20])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 667606708-(2-cyclopropylbenzyl)-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 467011018-(2-cyclopropylbenzyl)-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 29.2%

Procedure

8-(2-cyclopropylbenzyl)-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one (80 mg, 0.24 mmol) and 4-(4-methylpiperazino)aniline (45 mg, 0.24 mmol) were stirred at 140° C. for 3 h. After completion, the reaction mixture was purified by silica gel column chromatography using chloroform:methanol (100:3). The crude product was recrystallized from acetonitrile to give the title compound (31 mg, 0.07 mmol, 29%). ESMS m/z 467 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.53 (s, 1H), 7.60 (d, J=9.3 Hz, 1H), 7.14-7.20 (m, 2H), 6.99-7.13 (m, 4H), 6.71 (br. s., 2H), 6.63 (d, J=7.5 Hz, 1H), 6.54 (d, J=9.3 Hz, 1H), 5.72 (s, 2H), 3.12-3.18 (m, 4H), 2.54-2.64 (m, 4H), 2.36 (s, 3H), 2.00-2.11 (m, 1H), 0.90-0.99 (m, 2H), 0.69-0.77 (m, 2H).

Workup

  1. customAfter completion, the reaction mixture was purified by silica gel column chromatography
  2. customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-9720eddcf6284eccb0da68791a2e0809
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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