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

HRID 1806523Notes

Reaction equation

HRID 1806523 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.[C:21](OC(=O)C)(=[O:23])[CH3:22]>CN(C=O)C>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:22][C:21](=[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 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-6-[(2,6-difluorophenyl)amino]-2-(methylthio)-5-pyrimidinecarbaldehyde (200 mg, 0.63 mmol) in DMF (4.0 mL) and acetic anhydride (2.0 mL) was heated with a microwave (160° C.) for about 30 minutes. The resultant mixture was then concentrated. Flash chromatography (EtOAc/Hexane, 1:5) provided the title compound (109 mg, 51%): LC-MS m/z 340 (M+H)+.

Workup

  1. concentrationThe resultant mixture was then concentrated

Sources & evidence

ORD record
ord-4951dcf98b914643a286292e667ef4eb
Source dataset
uspto-grants-2013_01
Patent number
US08354416B2

Reaction notes

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