Dimethyl Sulfoxide → HCID 46701100, compound

HRID 1188719Notes

Reaction equation

HRID 1188719 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30](F)[C:3]=1[CH2:4][N:5]1[C:10]2[N:11]=[C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:13]=[CH:14][C:9]=2[CH:8]=[CH:7][C:6]1=[O:29].[CH3:35][S:36](C)=O>O>[F:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([S:36][CH3:35])[C:3]=1[CH2:4][N:5]1[C:10]2[N:11]=[C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:13]=[CH:14][C:9]=2[CH:8]=[CH:7][C:6]1=[O:29]

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 66760637HCID 66760637, compound

Product 1

HCID 46701100HCID 46701100, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-(2,6-difluorobenzyl)-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (23 mg, 0.05 mmol, Example 61) was treated with NaSMe (5 mg, 0.06 mmol) in DMSO (0.2 mL) at 100° C. for 2 h. The reaction mixture was diluted with water, the precipitated product was filtered off, then purified by silica gel column chromatography using dichloromethane:methanol (95:5) to give 8-(2-fluoro-6-(methylthio)benzyl)-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (22 mg, Y=90%). ESMS m/z 491 (M+H)+.

Workup

  1. filtrationthe precipitated product was filtered off
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e655299b72e449cfb143d6e058efc6bc
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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