Sodium hydride → 2-(Methoxymethyl)pyrimidine-4,6-diol

HRID 216237Notes

Reaction equation

HRID 216237 reaction equation
Cl.[CH3:2][O:3][CH2:4][C:5]([NH2:7])=[NH:6].C([C:10](CC)([C:14]([O-])=[O:15])[C:11]([O-])=[O:12])C.[H-].[Na+]>CCO>[CH3:2][O:3][CH2:4][C:5]1[N:7]=[C:11]([OH:12])[CH:10]=[C:14]([OH:15])[N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69515632,2-DiethylpropanedioateHCID 135486022-Methoxyethanimidamide hydrochloride

Product 1

HCID 1784946992-(Methoxymethyl)pyrimidine-4,6-diolYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methoxy-acetamidine hydrochloride (20.18 g, 0.16 mol) and diethylmalonate (24.6 mL, 0.16 mol) in EtOH (150 mL) is added 60% dispersion of sodium hydride in oil (14.3 g, 0.36 mol). The mixture is heated to reflux and stirred for 16 hours. The mixture is concentrated in vacuo and the residue is diluted with water (100 mL) and extracted with EtOAc (75 mL). The aqueous layer is acidified to pH 3 with HCl and extracted thrice with EtOAc (75 mL). The organic extracts from acidic solution are combined and dried over magnesium sulfate, filtered and concentrated to afford 2-methoxymethyl-pyrimidine-4,6-diol (20 g, 80%) as an oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. concentrationThe mixture is concentrated in vacuo
  4. additionthe residue is diluted with water (100 mL)
  5. extractionextracted with EtOAc (75 mL)
  6. extractionextracted thrice with EtOAc (75 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-52ced09d66ac43be8de11f6faa878e23
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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