Sodium ethoxide → HCID 86756058, compound

HRID 1858314Notes

Reaction equation

HRID 1858314 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[O-:14][CH2:15][CH3:16].[Na+]>C(O)C.[Na]>[CH2:15]([O:14][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1)[CH3:16]

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 86756058HCID 86756058, compoundYield 283%

Reagents, catalysts & solvents 2

HCID 5360545SodiumCatalystHCID 702EthanolSolvent

Procedure

An ice-cooled suspension of 50 g (215 mmol) of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate in 300 ml of ethanol was treated dropwise with a solution of sodium ethoxide (prepared from 5.1 g (222 mg.atom) of sodium and 300 ml of ethanol). After 1 hour the mixture was evaporated and the residue partitioned between 400 ml of dichloromethane and 400 ml of water. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 48 g (92%) of ethyl 4-ethoxy-2-methylthiopyrimidine-5-carboxylate as a colorless oil. [Mass spectrum (ESI) MH+ =243].

Workup

  1. customAfter 1 hour the mixture was evaporated
  2. customthe residue partitioned between 400 ml of dichloromethane and 400 ml of water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-e46563b7dd7c42518c2fd629310d8a9b
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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