Methyl chloroacetate → 2-(Chloromethyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1888338Notes

Reaction equation

HRID 1888338 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[N:17][C:16]1=[NH2+:23].[OH-].[Na+].CO[C:28](=O)[CH2:29][Cl:30]>CCO>[Cl:30][CH2:29][C:28]1[N:23]=[C:16]2[N:17]=[C:18]([CH3:22])[CH:19]=[C:20]([CH3:21])[N:15]2[N:14]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 14798Sodium HydroxideHCID 178425977HCID 178425977, compound

Product 1

HCID 455887142-(Chloromethyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidineYield 10.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-Amino-4,6-dimethyl-1H-pyrimidin-2-ylidene-ammonium 2,4,6-Trimethyl-benzenesulfonate (40 g, 0.1 mol) and NaOH (10 g, 0.2 mol) in 500 mL of EtOH was stirred at 50˜60° C. for 1 hour. After chloroacetic acid methyl ester (16.6 g, 0.15 mol) was added, the resultant mixture was stirred at reflux for 4 hours. After being concentrated under reduce pressure, the residue was diluted with water (1000 mL) and extracted with CH2Cl2 (300 mL×3). The combined organic layers were washed with brine (200 mL), dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=2/1) to give 2 g of 2-Chloromethyl-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine in 9% yield.

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationAfter being concentrated
  3. additionthe residue was diluted with water (1000 mL)
  4. extractionextracted with CH2Cl2 (300 mL×3)
  5. washThe combined organic layers were washed with brine (200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=2/1)

Sources & evidence

ORD record
ord-20b7e894b4564afdbc9c5409b72192c8
Source dataset
uspto-grants-2013_08
Patent number
US08501797B2

Reaction notes

Loading…