Triethylamine → HCID 755249, compound

HRID 842059Notes

Reaction equation

HRID 842059 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.Cl.CN.[CH2:22]([N:24](CC)CC)C>C(O)(C)C>[CH3:22][NH:24][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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 239537Ethyl 4-chloro-2-phenylpyrimidine-5-carboxylateHCID 6364545Methylamine hydrochloride

Product 1

HCID 755249HCID 755249, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate (10 g), methylamine hydrochloride (2.8 g), triethylamine (8.5 g) and isopropanol (100 ml) is refluxed for six hours. The reaction mixture is concentrated under reduced pressure, and to the residue are added chloroform and water. The chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from ethanol to give ethyl 4-methylamino-2-phenylpyrimidine-5-carboxylate (8 g).

Workup

  1. temperatureis refluxed for six hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionto the residue are added chloroform and water
  4. customThe chloroform layer is separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-14c226e23a12466ca13864c53b284880
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

Loading…