Methanol → 6-Ethylpyrimidin-4-ol

HRID 1916164Notes

Reaction equation

HRID 1916164 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4](S)[N:3]=1.CO>O.C(Cl)Cl.[Ni]>[CH2:8]([C:6]1[N:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=1)[CH3:9]

Participants

6

Reactant 2

HCID 887MethanolHCID 178436954HCID 178436954, compound

Product 1

HCID 1354076886-Ethylpyrimidin-4-olYield 98%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

90 g (0.58 mol) 4-Hydroxy-2-mercapto-6-ethyl pyrimidine and 270 g Raney-Nickel are suspended in water (1000 mL). The suspension is heated and stirred under reflux over night. Full conversion is detected by TLC (10% MeOH in DCM). The catalyst is filtered off over celite and the filtrate is evaporated to give crude product as a pale green solid (70.0 g; 98%). The product is used without further purification for the next step.

Workup

  1. temperatureThe suspension is heated
  2. temperatureunder reflux over night
  3. filtrationThe catalyst is filtered off over celite
  4. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-e767c86d60d240ed8c9c435bba23756c
Source dataset
uspto-grants-2013_12
Patent number
US08618111B2

Reaction notes

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