Glycine → HCID 22617810, compound

HRID 842061Notes

Reaction equation

HRID 842061 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[NH2:19][CH2:20][C:21]([OH:23])=[O:22].CN(C)C>C(O)C>[CH2:11]([O:10][C:8]([C:7]1[C:2]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[N:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][CH:6]=1)=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 750GlycineHCID 1146TrimethylamineHCID 239537Ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate

Product 1

HCID 22617810HCID 22617810, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate (21 g), glycine (6.6 g), trimethylamine (17.8 g) and ethanol (200 ml) is refluxed for four hours. The reaction mixture is concentrated under reduced pressure, and the residue is dissolved in water. To the mixture is added dropwise conc. hydrochloric acid under stirring at 0-5° C. until the value of the mixture is adjusted to pH 4. The precipitates are collected by filtration, and washed with water to give crude N-(5-ethoxycarbonyl-2-phenyl-4-pyrimidinyl)glycine (24 g).

Workup

  1. temperatureis refluxed for four hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in water
  4. additionTo the mixture is added dropwise conc. hydrochloric acid
  5. filtrationThe precipitates are collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-851684dc99394bbea9725373ff58d764
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

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