Acetic Acid → 2-Methoxy-4,6-dimethyl-5-pyrimidinol

HRID 2308140Notes

Reaction equation

HRID 2308140 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([O:10]CC2C=CC=CC=2)=[C:5]([CH3:18])[N:4]=1.[OH-].[K+].C(O)(=O)C>C(O)C.O>[CH3:1][O:2][C:3]1[N:4]=[C:5]([CH3:18])[C:6]([OH:10])=[C:7]([CH3:9])[N:8]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 22600728HCID 22600728, compound

Product 1

HCID 98128262-Methoxy-4,6-dimethyl-5-pyrimidinol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The 2-methoxy-4,6-dimethyl-5-benzyloxy pyrimidine 0.7 g (2.7 mmol) is dissolved in 10 ml of ethanol with 0.3 g (5.4 mmol) of KOH. The whole is refluxed for 11 hours, and after cooling the reaction is diluted with 20 ml of water and brought to pH 5 with glacial acetic acid. The mixture is extracted into ethyl acetate (3×25 ml), dried over Na2SO4 and stripped in vacuo. The resulting solid is purified by column chromatography on silica gel using 9:1 hexane:ethyl acetate as eluent. The yield is 0.4 g (98%).

Workup

  1. temperatureThe whole is refluxed for 11 hours
  2. temperatureafter cooling the reaction
  3. extractionThe mixture is extracted into ethyl acetate (3×25 ml)
  4. dry with materialdried over Na2SO4
  5. customThe resulting solid is purified by column chromatography on silica gel using 9:1 hexane

Sources & evidence

ORD record
ord-ea33df0bf8d84b15b583c7bf452cdeab
Source dataset
uspto-grants-2004_12
Patent number
US06835216B2

Reaction notes

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