Hydrochloric Acid → 2,4,6-Trimethyl-5-hydroxypyrimidine

HRID 2308138Notes

Reaction equation

HRID 2308138 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:8](=O)[CH3:9])=[C:5]([CH3:7])[N:6]=1.[OH-].[NH4+:12].Cl>>[CH3:1][C:2]1[N:12]=[C:8]([CH3:9])[C:4]([OH:3])=[C:5]([CH3:7])[N:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 3184185-Acetyl-2,4-dimethyloxazole

Product 1

HCID 1305522,4,6-Trimethyl-5-hydroxypyrimidineYield 60%

Procedure

The 2,4-dimethyl-5-acetyloxazole is poured into a Parr Bomb with 20 ml (51 mmol) of concentrated ammonium hydroxide and brought to 180° C. in three hours. Heating is continued for 10 hours, and after cooling the mixture is brought to pH 5 with HCl, extracted into ether, dried over Na2SO4 and stripped in vacuo. The residual solid is crystallized from benzene to give pale yellow crystals (1.3 g, 60%).

Workup

  1. temperatureHeating
  2. waitis continued for 10 hours
  3. temperatureafter cooling the mixture
  4. extractionextracted into ether
  5. dry with materialdried over Na2SO4
  6. customThe residual solid is crystallized from benzene

Sources & evidence

ORD record
ord-615019f15eda40c49d72965078351c7b
Source dataset
uspto-grants-2004_12
Patent number
US06835216B2

Reaction notes

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