HCID 19012233, compound → HCID 19012231, compound

HRID 1729237Notes

Reaction equation

HRID 1729237 reaction equation
[C:1]1([CH2:7][C:8]2[N:13]=[C:12]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=[C:10]([Cl:21])[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.O.[Pd]>[ClH:21].[C:1]1([CH2:7][C:8]2[NH:13][CH:12]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11][CH2:10][N:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 19012233HCID 19012233, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 19012231HCID 19012231, compoundYield 97.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of the 2,4-di(phenylmethyl)-6-chloropyrimidine (2.3 g, 7.81 mmol) obtained in (ii) in ethanol (50 ml) and water (5 ml) was hydrogenated at about 3 atmospheres in the presence of 10% palladium on charcoal catalyst (380 mg) until hydrogen uptake had ceased. After filtration through Hyflo (Trade mark; diatomaceous earth) to remove the catalyst, the solution was evaporated in vacuo. Addition of ethanol (50 ml) and evaporation followed by addition of toluene (50 ml) and evaporation afforded a white foam which was dried at 45° C., at a pressure of 20mmHg for 48 hours, to give 2.3 g 2,4-di(phenylmethyl)-3,4,5,6-tetrahydropyrimidine hydrochloride, m.pt., 50°-57° C. (deliquesces). M+ (-HCl) found: 264.

Workup

  1. filtrationAfter filtration through Hyflo (Trade mark; diatomaceous earth)
  2. customto remove the catalyst
  3. customthe solution was evaporated in vacuo
  4. additionAddition of ethanol (50 ml) and evaporation
  5. additionfollowed by addition of toluene (50 ml) and evaporation
  6. customafforded a white foam which
  7. customwas dried at 45° C., at a pressure of 20mmHg for 48 hours

Sources & evidence

ORD record
ord-ececd92e993642f89ebfa549be6bd34c
Source dataset
uspto-grants-1994_07
Patent number
US05332745

Reaction notes

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