HCID 86682825, compound → HCID 46941734, compound

HRID 1428179Notes

Reaction equation

HRID 1428179 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[C:11](SC)[N:10]=2)=[CH:5][CH:4]=1>[Ni].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[CH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 86682825HCID 86682825, compound

Product 1

HCID 46941734HCID 46941734, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of [4-(4-methoxyphenyl)-2-(methylsulfanyl)pyrimidin-5-yl]methanol (13.5 g), Raney-nickel (96 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 (8.6 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-0619a9e0ac3e4db4aa1de9e22a21cf7f
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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