Ethanol → Ethyl 2-chloropyrimidine-4-carboxylate

HRID 1628215Notes

Reaction equation

HRID 1628215 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.C(O)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 22509306Ethyl 2-chloropyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction mixture of 2-chloropyrimidine-4-carboxylic acid, 9.A (avialable from Anichem LLC, 1.00 g, 6.3 mmol), 1,3-dicyclohexylcarbodiimide (1.4 g, 6.9 mmol) and ethanol (0.32 g, 6.9 mmol) in DCM (10 ml) was stirred at room temperature overnight. The solid was filtrated off. DCM (80 ml) was added and washed with brine (30 ml) and dried over MgSO4. The solvent was evaporated. The crude product was purified by Cobi-Flash silica gel column to give 9.B. 0.74 g, yield, 63%. 1H NMR (400 MHz, chloroform-d) δ ppm 8.87 (1H, d, J=4.7 Hz), 7.95 (1H, d, J=4.7 Hz), 4.51 (2H, q, J=7.4 Hz), 1.45 (3H, t, J=7.0 Hz). MS ESI (pos.) m/e: 187.0 (M+H)+.

Workup

  1. filtrationThe solid was filtrated off
  2. additionDCM (80 ml) was added
  3. washwashed with brine (30 ml)
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated
  6. customThe crude product was purified by Cobi-Flash silica gel column

Sources & evidence

ORD record
ord-fe64970df30e4dc69b3cbb6be031370a
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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