HCID 46941731, compound → HCID 46941732, compound

HRID 1428176Notes

Reaction equation

HRID 1428176 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[C:10](SC)[N:9]=2)=[CH:4][CH:3]=1>[Ni].C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 46941731HCID 46941731, compound

Product 1

HCID 46941732HCID 46941732, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of [4-(4-fluorophenyl)-2-(methylsulfanyl)pyrimidin-5-yl]methanol (10.3 g), Raney-nickel (77 g) and ethanol (500 mL) was heated under reflux for 2 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (4.8 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-6b22652c935240fc86506e06674a6b8d
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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