Diethyl allylmalonate → 5-Allylpyrimidine-4,6-diol

HRID 82247

Reaction equation

HRID 82247 reaction equation
C([O:3][C:4](=O)[CH:5]([CH2:11][CH:12]=[CH2:13])[C:6](OCC)=[O:7])C.C[O-].[Na+].C(O)(=O)C.[CH:22]([NH2:24])=[NH:23]>C(O)C>[CH2:11]([C:5]1[C:6](=[O:7])[NH:24][CH:22]=[N:23][C:4]=1[OH:3])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 74900Diethyl allylmalonateHCID 160693Formamidine acetateHCID 10942334Sodium Methoxide

Product 1

HCID 254215755-Allylpyrimidine-4,6-diolYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Allyl-malonic acid diethyl ester (Preparation 205, 100 g, 0.5 mol) was added dropwise to a mixture of sodium methoxide (27 g, 0.5 mol) in ethanol (1 L) at 0-5° C. and the mixture was stirred at this temperature for 10 min. Formamidine acetate (51.9 g, 0.5 mol) was added and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo, and aqueous hydrochloric acid (36.5%) and water were added to adjust the pH to approximately 3 at 0-20° C. The resulting mixture was filtered to afford the title compound as a colorless solid in 57% yield, 87.12 g.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvent was removed in vacuo, and aqueous hydrochloric acid (36.5%) and water
  3. additionwere added
  4. customat 0-20° C
  5. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-8d9eb956cc6845f2a0afad3fa487d257
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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