Sodium Hydroxide → HCID 11694935, compound

HRID 1374732Notes

Reaction equation

HRID 1374732 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:15]=[CH:14][N:13]=[C:12]([C:16]([O:18]C)=[O:17])[CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH3:22].[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:15]=[CH:14][N:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH3:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12997477HCID 12997477, compound

Product 1

HCID 11694935HCID 11694935, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

8.75 g (0.02 mol) of methyl 6-(4-fluoro-3-methylbenzylcarbamoyl)pyrimidine-4-carboxylate (70%) were taken up in 150 ml of ethanol, after which 1.89 g (0.022 mol) of NaOH in 6 ml of water were added. After 3 hours (h) at room temperature, the solvent was removed under reduced pressure and water was added to the residue; the solution was then brought to pH <2 with conc. HCl. The precipitate was filtered off with suction and dried. This resulted in 5.5 g (94%) of 6-(4-fluoro-3-methylbenzylcarbamoyl)pyrimidine-4-carboxylic acid. MS (ES+): m/e=289.09.

Workup

  1. customthe solvent was removed under reduced pressure and water
  2. additionwas added to the residue
  3. filtrationThe precipitate was filtered off with suction
  4. customdried
  5. customThis resulted in 5.5 g (94%) of 6-(4-fluoro-3-methylbenzylcarbamoyl)pyrimidine-4-carboxylic acid

Sources & evidence

ORD record
ord-c222043a826443c7bc577244b927bb15
Source dataset
uspto-grants-2007_01
Patent number
US07166609B2

Reaction notes

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