Ethanol → Ethyl 2-chloropyrimidine-4-carboxylate

HRID 62867Notes

Reaction equation

HRID 62867 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[CH:11]1(N=C=NC2CCCCC2)CCCC[CH2:12]1.CCO>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:11]([O:9][C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)=[O:10])[CH3:12]

Participants

6

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 221357512-Chloropyrimidine-4-carboxylic acid

Product 1

HCID 22509306Ethyl 2-chloropyrimidine-4-carboxylateYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

After 2-chloropyrimidin-4-carboxylic acid (0.223 g, 1.4 mmol) was dissolved in DCM (7 mL), dicyclohexylcarbodiimide (0.29 g, 1.4 mmol), DMAP (0.017 g, 0.14 mmol) and EtOH (0.1 mL, 1.4 mmol) were added thereto, and the mixture was stirred at room temperature for 24 hours. After the termination of the reaction, the reactant was filtered and separated by column chromatography to obtain the title compound (0.13 g, 50%).

Workup

  1. customAfter the termination of the reaction
  2. filtrationthe reactant was filtered
  3. customseparated by column chromatography

Sources & evidence

ORD record
ord-af750f0748e5405d9d45dd0a15e53603
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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