Dimethyl malonate → HCID 178437790, compound

HRID 1589630Notes

Reaction equation

HRID 1589630 reaction equation
C[O-].[Na+].Cl.[C:5]([NH2:9])(=[NH:8])[CH2:6][CH3:7].[C:10](OC)(=[O:16])[CH2:11][C:12](OC)=[O:13]>CO>[OH:13][C:12]1[CH:11]=[C:10]([OH:16])[N:9]=[C:5]([CH2:6][CH3:7])[N:8]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 12301253Propionimidamide hydrochloride

Product 1

HCID 178437790HCID 178437790, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a cooled (using an ice-bath), stirred solution of 25% sodium methoxide (1200 ml, 5.55 mole) was added a slurry of 200 g (1.85 mole) of propionamidine hydrochloride in 300 ml methanol. Next, 244 g (1.85 mole) of dimethyl malonate was added and the mixture was permitted to warm to about 20° C., after which it was stirred for 16 hours. The mixture was evaporated in vacuo and water (about 2 l) was then added. This mixture was neutralized with concentrated hydrochloric acid to provide a white precipitate which was separated by filtration to provide 230 g (96%) of 4,6-dihydroxy-2-ethylpyrimidine, m.p. 312°-315° C. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperatureTo a cooled (using an ice-bath)
  2. customThe mixture was evaporated in vacuo and water (about 2 l)
  3. additionwas then added
  4. customto provide a white precipitate which
  5. customwas separated by filtration

Sources & evidence

ORD record
ord-580bd4959747401eac443072a96b195a
Source dataset
uspto-grants-1986_02
Patent number
US04572910

Reaction notes

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