Potassium Hydroxide → 2-(N-Ethoxycarbonyl-N-propargylaminomethyl)-pyrimidine

HRID 1491652Notes

Reaction equation

HRID 1491652 reaction equation
[CH2:1]([NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8])[C:2]#[CH:3].[OH-].[K+].Cl[CH2:13][C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C1(C)C=CC=CC=1>[CH2:7]([O:6][C:5]([N:4]([CH2:13][C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH2:1][C:2]#[CH:3])=[O:9])[CH3:8]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 12155513Ethyl N-propargylcarbamateHCID 128773712-(Chloromethyl)pyrimidine

Product 1

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

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

11.5 g (91 mmol) of ethyl N-propargylcarbamate are introduced into 90 ml of toluene, 20.3 g of KOH powder and 0.5 g of triethylbenzylammonium chloride are added, and 13.5 g (104 mmol) of 2-chloromethyl-pyrimidine (German Offenlegungsschrift 2,932,643) are added dropwise at room temperature. The mixture is stirred overnight at room temperature, the salts are filtered off with suction, the filtrate is washed using saturated sodium chloride solution, dried over magnesium sulphate and concentrated, and the concentrate is distilled.

Workup

  1. additionare added
  2. filtrationthe salts are filtered off with suction
  3. washthe filtrate is washed
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. distillationthe concentrate is distilled

Sources & evidence

ORD record
ord-f56dcc419042420997d49f8792098b97
Source dataset
uspto-grants-1994_12
Patent number
US05371090

Reaction notes

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