Water → HCID 178429343, compound

HRID 1501101Notes

Reaction equation

HRID 1501101 reaction equation
O=[C:2]([CH3:9])[CH2:3][C:4]([O:6]CC)=O.Cl.[C:11](=[NH:14])([NH2:13])[CH3:12].C([O-])C.[Na+].O>C(O)C>[CH3:12][C:11]1[N:14]=[C:4]([OH:6])[CH:3]=[C:2]([CH3:9])[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 178429343HCID 178429343, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-oxobutanoate (10.0 g, 77 mmol) and acetimidamide hydrochloride (7.23 g, 77 mmol) were added to the solution of sodium ethanolate (10.5 g, 154 mmol) in ethanol (200 mL). And the mixture was refluxed for 20 hours. Water (10 mL) was added to the mixture. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give 2,6-dimethylpyrimidin-4-ol as a yellow solid (3.43 g, 36%). LRMS (M+H) m/z: calcd 124.06. found 124.

Workup

  1. temperatureAnd the mixture was refluxed for 20 hours
  2. concentrationThe resultant mixture was concentrated
  3. customto give a residue
  4. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-49d1fdb6d05b4a83a55c979cfb091863
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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