HCID 178440259, compound → HCID 178440189, compound

HRID 1708415Notes

Reaction equation

HRID 1708415 reaction equation
[CH2:1]([C:4]1[N:9]=[C:8](SC)[N:7]=[C:6]([OH:12])[C:5]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1)[CH2:2][CH3:3]>COCCOCCOC.[Ni]>[CH2:1]([C:4]1[N:9]=[CH:8][N:7]=[C:6]([OH:12])[C:5]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 178440259HCID 178440259, compound

Product 1

HCID 178440189HCID 178440189, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8150DiglymeSolvent

Procedure

29 g of 6-n-propyl-2-methylthio-4-hydroxy-5-[(2'-cyano-4-biphenylyl)methyl]pyrimidine, prepared in Example 101, are dissolved in 250 ml of diglyme, and 60 g of Raney nickel are added. The mixture is heated to reflux for 3 hours. The catalyst is filtered off and washed with ethanol, the filtrate is evaporated under vacuum and the residue is chromatographed on silica gel in a 2:8 acetone/chloroform eluent to give 14.2 g of 6-n-propyl-4-hydroxy-5-[(2'-cyano-4-biphenylyl)methyl]pyrimidine in the form of crystals of melting point 158° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe catalyst is filtered off
  4. washwashed with ethanol
  5. customthe filtrate is evaporated under vacuum
  6. customthe residue is chromatographed on silica gel in a 2:8 acetone/chloroform eluent

Sources & evidence

ORD record
ord-9754f6eb072e4d9cb1e15f265f541381
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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