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

HRID 1735958Notes

Reaction equation

HRID 1735958 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 (1.0 g, 0.0047 mol) was suspended in 2M sodium hydroxide (15 ml), boiled for 10 min. 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. extractionThe solution was extracted with ethyl acetate (10×25 ml)
  2. extractionThe organic phase was extracted with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness, in vacuo

Sources & evidence

ORD record
ord-43cf43085f6e48fa965cb4696f8bb1ee
Source dataset
uspto-grants-1996_07
Patent number
US05539082

Reaction notes

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