Water → HCID 13385963, compound

HRID 851314Notes

Reaction equation

HRID 851314 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](Cl)[CH:6]=[CH:5][N:4]=1.[OH-].[Na+].[CH2:12]([OH:15])[C:13]#[CH:14].O>C1C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:15][CH2:12][C:13]#[CH:14])[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 14798Sodium HydroxideHCID 971134-Chloro-2-methylthiopyrimidine

Product 1

HCID 13385963HCID 13385963, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 241BenzeneSolvent2×

Procedure

3 grams of 2-methylthio-4-chloro pyrimidine in 30 ml of benzene was reacted with 3 ml of an aqueous 40% sodium hydroxide solution, 0.3 grams of triethyl benzyl ammonium chloride and 2 ml of propargyl alcohol. The resultant reaction mixture was refluxed with stirring for a period of 4 hours. Following, the mixture was cooled and 20 milliliters of water added, so resulting in separation of the benzene layer. Then, the solvent was evaporated under reduced pressure to yield 4.1 grams of 2-methylthio-4-propargyloxy pyrimidine melting at a temperature within the range of 70°-71° C. in ethanol.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas refluxed
  3. temperaturethe mixture was cooled
  4. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e7bfc19787054603ac7c7efbb7bd6b49
Source dataset
uspto-grants-1983_05
Patent number
US04384118

Reaction notes

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