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

HRID 1957745Notes

Reaction equation

HRID 1957745 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 2M 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 C8 H10N2O4, 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-893418337d1b40fab056dd62141fea6e
Source dataset
uspto-grants-1998_07
Patent number
US05786461

Reaction notes

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