Acetic Anhydride → 4-Chloro-2-methylsulfanyl-8-(2,6-difluorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1454444Notes

Reaction equation

HRID 1454444 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6]([NH:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[F:18])[N:5]=[C:4]([S:19][CH3:20])[N:3]=1.[CH3:21][C:22](OC(C)=O)=[O:23]>CN(C=O)C>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:21][C:22](=[O:23])[N:10]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[F:18])[C:6]=2[N:5]=[C:4]([S:19][CH3:20])[N:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 99447374-Chloro-6-((2,6-difluorophenyl)amino)-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 119515134-Chloro-2-methylsulfanyl-8-(2,6-difluorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-Chloro-6-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde (200 mg, 0.63 mmol) in DMF (4.0 mL) and Ac2O (2.0 mL) was heated with “Smith Creator” (microwave, 160° C.) for 30 minutes. The mixture was concentrate under vacuum. Flash chromatography (EtOAc/Hexane, 1:5) then provided the title compound (50%): MS (ES) m/z 340 (M+H)+; 1H-NMR(CDCl3) δ 2.24 (s, 3H), 6.80 (d, J=9.8 Hz, 1H), 7.12 (m, 2H), 7.49 (m, 1H), 8.04 (d, J=9.8 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrate under vacuum

Sources & evidence

ORD record
ord-4f35ef0bc3c744bc9200c1d768c51065
Source dataset
uspto-grants-2009_01
Patent number
US07479558B2

Reaction notes

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