1-Butanol → HCID 23020127, compound

HRID 917396Notes

Reaction equation

HRID 917396 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[OH-].[K+].CS([C:12]1[N:17]=[C:16]([CH3:18])[C:15]([C:19]([O:21]CC)=[O:20])=[CH:14][N:13]=1)(=O)=O>O>[CH2:1]([O:5][C:12]1[N:17]=[C:16]([CH3:18])[C:15]([C:19]([OH:21])=[O:20])=[CH:14][N:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-Butanol2×HCID 14797Potassium HydroxideHCID 23020175Ethyl 4-methyl-2-(methylsulfonyl)pyrimidine-5-carboxylate

Product 1

HCID 23020127HCID 23020127, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.5 ml of butanol, 0.72 g (11 mmol) of 85.5% potassium hydroxide powder was suspended, followed by drop-wise adding, under ice-cooling, a 1.5 ml of butanol solution dissolving with 1.22 g (5.0 mmol) of ethyl 2-methansulfonyl-4-methylpyrimidine-5-carboxylate. After the end of the drop-wise addition, the solution was stirred at room temperature for 3 hours. To the reaction liquid, 50 ml of water was added, and the water layer was washed with diisopropyl ether, followed by adding 10% hydrochloric acid to make acidic, and extracting with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to obtain 0.87 g (yield: 83%) of 2-butoxy-4-methylpyrimidine-5-carboxylic acid.

Workup

  1. additionadding, under ice-
  2. temperaturecooling
  3. additionAfter the end of the drop-wise addition
  4. additionwas added
  5. washthe water layer was washed with diisopropyl ether
  6. additionby adding 10% hydrochloric acid
  7. extractionextracting with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materiala saturated saline solution in this order, and dried over anhydrous magnesium sulfate
  10. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-568b65bf71284c71b827e97deece46a9
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

Loading…