Methanol → 6-Ethylpyrimidin-4-ol

HRID 632875Notes

Reaction equation

HRID 632875 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-cb7a2117575048a8ad682f99f5223ff4
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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