Triethylamine → 2-Ethoxycarbonylaminomethyl-pyrimidine

HRID 1033751Notes

Reaction equation

HRID 1033751 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][C:10]1[N:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH2:16]([O:18][C:19](Cl)=[O:20])[CH3:17]>C1(C)C=CC=CC=1>[CH2:16]([O:18][C:19]([NH:8][CH2:9][C:10]1[N:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 46580472-Pyrimidinemethanamine

Product 1

HCID 189536352-Ethoxycarbonylaminomethyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

49.5 g (0.49 mol) of triethylamine are added to 49.5 g (0.45 mol) of 2-aminomethyl-pyrimidine in 450 ml of toluene and then 52 g (0.48 mol) of ethyl chlorocarbonic acid are added dropwise under cooling with ice. The mixture is subsequently stirred at room temperature for 2 hours. Triethylamine hydrochloride is filtered off with suction, the filtrate is washed with brine, dried with MgSO4, concentrated, and distilled.

Workup

  1. temperatureunder cooling with ice
  2. filtrationTriethylamine hydrochloride is filtered off with suction
  3. washthe filtrate is washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-5b87c8e40bf3472fa51922030f5f156a
Source dataset
uspto-grants-1994_05
Patent number
US05312823

Reaction notes

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