Acetone → 2-Butoxy-4-methylpyrimidine-5-carboxylic acid

HRID 917395Notes

Reaction equation

HRID 917395 reaction equation
CC(C)=O.[CH2:5]([O:9][C:10]1[N:15]=[C:14]([CH3:16])[C:13]([C:17]([O:19]CC)=[O:18])=[CH:12][N:11]=1)[CH2:6][CH2:7][CH3:8].[OH-].[Na+]>O>[CH2:5]([O:9][C:10]1[N:15]=[C:14]([CH3:16])[C:13]([C:17]([OH:19])=[O:18])=[CH:12][N:11]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 23020362Ethyl 2-butoxy-4-methylpyrimidine-5-carboxylate

Product 1

HCID 230201272-Butoxy-4-methylpyrimidine-5-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of acetone, 10.0 g (42 mmol) of ethyl 2-butoxy-4-methylpyrimidine-5-carboxylate was dissolved, followed by adding 50 ml of water, then adding drop-wise 13.4 g (84 mmol) of a 25% sodium hydroxide aqueous solution, and stirring at room temperature for 1 hour. The reaction liquid was concentrated at 40° C. under reduced pressure to remove acetone, and 10% hydrochloric acid was added to make acidic. The crystal precipitated was filtered, washed with water and dried to obtain 8.00 g (yield: 91%) of 2-butoxy-4-methylpyrimidine-5-carboxylic acid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated at 40° C. under reduced pressure
  3. customto remove acetone, and 10% hydrochloric acid
  4. additionwas added
  5. customThe crystal precipitated
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-ff12b6f4510a40c69c6dbca4d7f52df6
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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