Sodium ethoxide → 5-Methylpyrimidine-4,6-diol

HRID 729745Notes

Reaction equation

HRID 729745 reaction equation
CC[O-].[Na+].Cl.[CH:6]([NH2:8])=[NH:7].C[CH2:10][CH:11]([C:16](OCC)=[O:17])[C:12](OC)=[O:13]>C(O)C>[OH:13][C:12]1[C:11]([CH3:10])=[C:16]([OH:17])[N:8]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5088009HCID 5088009, compoundHCID 10313058Methanimidamide, hydrochloride (1:1)

Product 1

HCID 1784317855-Methylpyrimidine-4,6-diolYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
0 °C

Procedure

102 ml (282 mmoles) of a solution of sodium ethylate at 21% in ethanol is added to a solution of 7.5 g (94 mmoles) of formamidine hydrochloride in 250 ml of ethanol cooled down to 0° C. and the mixture is stirred for 30 minutes; then a solution of 13 ml (94 mmoles) of diethyl methyl malonate in 50 ml of ethanol is added followed by stirring overnight at ambient temperature. The reaction mixture is evaporated to dryness under reduced pressure (2 kPa) and the residue is taken up in ethyl acetate, water and acetic acid in order to adjust the pH to 6. The precipitate is filtered then washed successively with water, isopropanol, diethyl ether and finally with pentane. 7 g (Yield=60%) of expected product is obtained in the form of a beige solid.

Workup

  1. stirringby stirring overnight at ambient temperature
  2. customThe reaction mixture is evaporated to dryness under reduced pressure (2 kPa)
  3. filtrationThe precipitate is filtered
  4. washthen washed successively with water, isopropanol, diethyl ether and finally with pentane

Sources & evidence

ORD record
ord-d1f730b294bf47f4945592b6fd621240
Source dataset
uspto-grants-2009_09
Patent number
US07582640B2

Reaction notes

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