Triethylamine → Ethyl pyrimidine-4-carboxylate

HRID 1671484Notes

Reaction equation

HRID 1671484 reaction equation
C(N(CC)CC)C.Cl[C:9]1[N:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[C:11](Cl)[N:10]=1>O1CCCC1.[C].[Pd]>[N:10]1[CH:11]=[CH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:14][CH:9]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 13341900Ethyl 2,6-dichloropyrimidine-4-carboxylate

Product 1

HCID 13639438Ethyl pyrimidine-4-carboxylateYield 86,605.898%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (48.03 g, 0.475 mmol) was added to a solution of ethyl 2,6-dichloropyrimidine-4-carboxylate (38.60 g, 0.175 mmol) in tetrahydrofuran (700 ml). 5% Palladium-carbon was added and the mixture was stirred under a hydrogen atmosphere for 6 hrs. The solid in the reaction system was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give ethyl pyrimidine-4-carboxylate (23.06 g, 87%).

Workup

  1. customThe solid in the reaction system was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-24f2128d00ad456281ea50007689b28a
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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