Propargyl bromide → 2-(N-Ethoxycarbonyl-N-propargylaminomethyl)-pyrimidine

HRID 1491658Notes

Reaction equation

HRID 1491658 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH2:7][C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:5])[CH3:2].[OH-].[K+].[CH2:16](Br)[C:17]#[CH:18]>[Br-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]([CH2:7][C:8]1[N:9]=[CH:10][CH:11]=[CH:12][N:13]=1)[CH2:18][C:17]#[CH:16])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 14797Potassium HydroxideHCID 189536352-Ethoxycarbonylaminomethyl-pyrimidine

Product 1

HCID 189536422-(N-Ethoxycarbonyl-N-propargylaminomethyl)-pyrimidine

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 1140TolueneSolvent

Procedure

18.1 g (0.1 mol) of 2-ethoxycarbonylaminomethyl-pyrimidine are added to a suspension of 20 g (0.3 mol) of pulverized KOH and 1.1 g (5 mmol) of triethylbenzylammoniumbromide in 200 g of toluene, and then 18 g (0.12 mol) of propargylbromide (80% solution in toluene) at room temperature. The mixture is subsequently stirred for 15 hours at room temperature, the salts are filtered off with suction, the filtrate is washed with brine, dried with MgSO4 concentrated and distilled. The reaction product is identical with that of example Z1b.

Workup

  1. customat room temperature
  2. filtrationthe salts are 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-89c12a1173a14250b66b3380993ddc4c
Source dataset
uspto-grants-1994_12
Patent number
US05371090

Reaction notes

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