Water → HCID 13385964, compound

HRID 851315Notes

Reaction equation

HRID 851315 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](Cl)[C:6]([O:10][CH2:11][CH3:12])=[CH:5][N:4]=1.[NH2-].[Na+].[CH2:15]([OH:18])[C:16]#[CH:17].O>C1C=CC=CC=1>[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:18][CH2:15][C:16]#[CH:17])[C:6]([O:10][CH2:11][CH3:12])=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 24533Sodium amide2×HCID 20502176HCID 20502176, compound

Product 1

HCID 13385964HCID 13385964, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution comprising 3 grams of 2-methylthio-4-chloro-5 ethoxy pyrimidine in 30 milliliters of benzene was treated with 1 gram of sodium amide and 1.5 ml of propargyl alcohol. The reaction mixture was refluxed with stirring for 5 hours. Upon cooling, the unreacted sodium amide was decomposed with water, the benzene layer separated and the solvent evaporated under reduced pressure. Crystallization of the residue from ethanol yielded 2.8 grams of 2-methylthio-4-propargyloxy-5-ethoxy pyrimidine having a melting point ranging from 84°-85° C.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperatureUpon cooling
  3. customthe benzene layer separated
  4. customthe solvent evaporated under reduced pressure
  5. customCrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-dfd1ef83d4de4535a763a2efba045c7d
Source dataset
uspto-grants-1983_05
Patent number
US04384118

Reaction notes

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