Fluorine → 1-(2-Chloro-5-fluoropyrimidin-4-yl)ethanone

HRID 1400179Notes

Reaction equation

HRID 1400179 reaction equation
BrCC(C1C=CN=C(Cl)C=1)=O.ClC1C=C(C(=O)C)C=CN=1.ClC1C=C(C#N)C=CN=1.BrCC(C1C=CN=C(SC)N=1)=O.OOS([O-])=O.[K+].FF.Br[CH2:52][C:53]([C:55]1[C:60]([F:61])=[CH:59][N:58]=[C:57]([Cl:62])[N:56]=1)=[O:54]>>[Cl:62][C:57]1[N:56]=[C:55]([C:53](=[O:54])[CH3:52])[C:60]([F:61])=[CH:59][N:58]=1

Participants

8

Reactant 7

HCID 24524FluorineHCID 5686382-Chloro-4-cyanopyridineHCID 131452551-(2-Chloropyridin-4-yl)ethan-1-oneHCID 167204312-Bromo-1-(2-chloropyridin-4-yl)ethanoneHCID 23707502Potassium hydroxy sulfiteHCID 426090692-Bromo-1-(2-(methylthio)pyrimidin-4-yl)ethanoneHCID 865947392-Bromo-1-(2-chloro-5-fluoropyrimidin-4-yl)ethanone

Product 1

HCID 865947381-(2-Chloro-5-fluoropyrimidin-4-yl)ethanone

Procedure

Halopyridine 9, wherein L is halogen (9A) may be obtained, for example, from 2-bromo-1-(2-chloro-pyridin-4-yl)-ethanone prepared by halogenation of 1-(2-chloropyridin-4-yl)ethanone, obtainable from 2-chloro-4-cyano pyridine, as described in J. Het. Chem., 1983, 20, 533. 1-[2-(Methylthio)pyrimidin-4-yl] derivative 9, wherein L is CH3—S— (9B), obtainable from 2-bromo-1-(2-methylsulfanyl-pyrimidin-4-yl)-ethanone (described in WO03/011838), may be activated to the corresponding sulfoxide or sulfone 9, wherein L is CH3—S(O)— or CH3—S(O)2— (9D), by oxidation, for example with oxone. Halopyrimidine derivative 9, wherein L is halogen and R5 is fluorine (9C), may be instead prepared from 2-bromo-1-(2-chloro-5-fluoropyrimidin-4-yl)ethanone, obtained by halogenation of 1-(2-chloro-5-fluoropyrimidin-4-yl)ethanone, in turn prepared as described in WO04/058762.

Sources & evidence

ORD record
ord-e791323cb8564ab0b8116ec951cd20d0
Source dataset
uspto-grants-2014_12
Patent number
US08906934B2

Reaction notes

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