Triethylamine → Ethyl pyrimidine-4-carboxylate

HRID 1896160Notes

Reaction equation

HRID 1896160 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-carboxylate2×

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 (intermediate 4, 38.60 g, 0.175 mmol) in tetrahydrofuran (700 ml). The solution was added with Palladium-carbon (5%), and stirred under a hydrogen atmosphere for 6 hours. 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 (intermediate 5, 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-bda6a4514bc64fac88c6b05e2db53d9d
Source dataset
uspto-grants-2013_08
Patent number
US08518939B2

Reaction notes

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