2-(Methylthio)-4-(tributylstannyl)pyrimidine → [6-(2,4-Difluoro-phenylamino)-pyridin-3-yl]-[2-methoxy-5-(2-methylsulfanyl-pyrimidin-4-yl)-phenyl]-methanone

HRID 896086

Reaction equation

HRID 896086 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:14][CH:15]=2)=[O:9])[CH:7]=1.[CH3:27][S:28][C:29]1[N:34]=[C:33]([Sn](CCCC)(CCCC)CCCC)[CH:32]=[CH:31][N:30]=1>>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:13]1[N:12]=[CH:11][C:10]([C:8]([C:6]2[CH:7]=[C:2]([C:31]3[CH:32]=[CH:33][N:34]=[C:29]([S:28][CH3:27])[N:30]=3)[CH:3]=[CH:4][C:5]=2[O:25][CH3:26])=[O:9])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 22349594(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone

Product 1

HCID 22349580[6-(2,4-Difluoro-phenylamino)-pyridin-3-yl]-[2-methoxy-5-(2-methylsulfanyl-pyrimidin-4-yl)-phenyl]-methanoneYield 45%

Procedure

[6-(2,4-Difluoro-phenylamino)-pyridin-3-yl]-[2-methoxy-5-(2-methylsulfanyl-pyrimidin-4-yl)-phenyl]-methanone is prepared in analogy to example 11 from (5-bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone and 2-methylsulfanyl-4-tributylstannanyl-pyrimidine in 45% yield:

Sources & evidence

ORD record
ord-1eebe55b109b43398c3ca6b4e770e79f
Source dataset
uspto-grants-2005_07
Patent number
US06919336B2

Linked notes

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