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Dimethyl Sulfoxide → 2-Pyrimidineacetic acid ethyl ester

HRID 1907676
Notes
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Reaction equation

HRID 1907676 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7](C(OCC)=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].CS(C)=O.[Cl-].[Na+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 2303274Diethyl (pyrimidin-2-yl)propanedioate

Product 1

HCID 123671052-Pyrimidineacetic acid ethyl esterYield 63.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
142.5 °C

Procedure

4.76 g of diethyl (2-pyrimidinyl)malonate and 20 ml of dimethyl sulfoxide were mixed. To the mixture was added 1.40 g of sodium chloride and 0.72 g of water. The mixture was stirred for about 20 minutes at an inner temperature of 140 to 145° C., and for about 20 minutes at an inner temperature of 145 to 148° C. The mixture was allowed to cool to room temperature, then, to the reaction mixture was added water, and extracted with ethyl acetate. The organic layer was washed with saturated brine twice, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure to obtain 2.12 g of ethyl (2-pyrimidinyl)acetate.

Workup

  1. waitfor about 20 minutes at an inner temperature of 145 to 148° C
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine twice
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a5fcd2cabd048ffb1528e6dd563e24a
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598176B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes