Hydrochloric Acid → 3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoic acid

HRID 1166442Notes

Reaction equation

HRID 1166442 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][CH2:5][N:6]1[CH:14]=[C:12]([CH3:13])[C:10](=[O:11])[NH:9][C:7]1=[O:8].Cl>[OH-].[Na+]>[N:6]1([CH2:5][CH2:4][C:3]([OH:15])=[O:2])[CH:14]=[C:12]([CH3:13])[C:10](=[O:11])[NH:9][C:7]1=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15138291ThyPropOate

Product 1

HCID 15195633-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3-(1-Thyminyl)propanoic acid methyl ester (1 g, 0.0047 mol) was suspended in 2 M sodium hydroxide (15 mL), refluxed for 10 minutes. The pH was adjusted to 0.3 with conc. hydrochloric acid. The solution was extracted with ethyl acetate (10×25 mL). The organic phase was extracted with saturated aqueous sodium chloride, dried over magnesium sulfate, and evaporated to dryness in vacuo, to give the title compound as a white solid (0.66 g, 71%). M.p. 118-121° C. Anal. for C8H10N2O4, found (calc.) C, 48.38 (48.49); H, 5.09 (5.09); N, 13.93 (14.14). The compound showed satisfactory 1H and 13C-NMR spectra.

Workup

  1. temperaturerefluxed for 10 minutes
  2. extractionThe solution was extracted with ethyl acetate (10×25 mL)
  3. extractionThe organic phase was extracted with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-42a49e835a2a46eba6d62e819338b809
Source dataset
uspto-grants-2003_09
Patent number
US06613873B1

Reaction notes

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