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

HRID 2110765Notes

Reaction equation

HRID 2110765 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-69fc7366e8f34b179392d1e4d6f74920
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

Loading…