HCID 53945835, compound → HCID 15171492, compound

HRID 728119Notes

Reaction equation

HRID 728119 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[C:9]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[H][H]>C(O)C.O1CCCC1.[Pd]>[C:1]([NH:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 53945835HCID 53945835, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15171492HCID 15171492, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-acetamido-4-[2-(4-nitrophenyl)vinyl]pyrimidine (8.52 g) in ethanol (200 ml) and tetrahydrofuran (100 ml) was hydrogenated over 10% palladium on carbon (2 g) under atmospheric pressure of hydrogen gas for 6 hours at ambient temperature. The catalyst was removed by filtration and the filtrate was evaporated in vacuo to give a crystalline residue, which was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 2-acetamido-4-[2-(4-aminophenyl)ethyl]pyrimidine (7.0 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customto give a crystalline residue, which
  4. customwas recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-d82edc999328491b9a8427240e06af73
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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