Ethanol → Sodium pyrimidine-2-carboxylate

HRID 23724Notes

Reaction equation

HRID 23724 reaction equation
C(C1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#N.[OH-:9].[Na+:10].[CH2:11]([OH:13])[CH3:12]>O>[N:8]1[CH:7]=[CH:6][CH:5]=[N:4][C:12]=1[C:11]([O-:9])=[O:13].[Na+:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 27579792-Cyanopyrimidine

Product 1

HCID 23677639Sodium pyrimidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
55 °C

Procedure

To a slurry of 2-cyanopyrimidine (50 g) in water (100 ml) at 2° C. was added a solution of sodium hydroxide (50 wt %, 45.6 g) in water (30 ml) with an exotherm to 50° C. The mixture was stirred at 55° C. for 2 h, ethanol (500 ml) was added and the mixture concentrated in vacuo to an oil. Ethanol (250 ml) was added and the mixture concentrated to a paste. Ethanol (250 ml) was added and the mixture stirred at 15-20° C. for 30 min. The precipitate was collected by vacuum filtration, washed with ethanol (100 ml) and dried in a 75° C. vacuum oven to afford 67.57 g of the title compound as a white solid.

Workup

  1. concentrationthe mixture concentrated in vacuo to an oil
  2. additionEthanol (250 ml) was added
  3. concentrationthe mixture concentrated to a paste
  4. additionEthanol (250 ml) was added
  5. stirringthe mixture stirred at 15-20° C. for 30 min
  6. filtrationThe precipitate was collected by vacuum filtration
  7. washwashed with ethanol (100 ml)
  8. customdried in a 75° C. vacuum oven

Sources & evidence

ORD record
ord-eed4ec63484e46889df3f90095108f6e
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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