Thymine → ThyPropOate

HRID 861289Notes

Reaction equation

HRID 861289 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].[OH-].[Na+]>CO>[CH3:15][O:14][C:10](=[O:13])[CH2:11][CH2:12][N:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3]

Participants

5

Reactant 3

HCID 1135ThymineHCID 7294Methyl AcrylateHCID 14798Sodium Hydroxide

Product 1

HCID 15138291ThyPropOate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thymine (14 g, 0.11 mol) was suspended in methanol. Methyl acrylate (39.6 mL, 0.44 mol) was added, along with catalytic amounts of sodium hydroxide. The solution was refluxed in the dark for 45 h, evaporated to dryness in vacuo, and the residue dissolved in methanol (8 mL) with heating. After cooling in an ice bath, the product was precipitated by addition of ether (20 mL), isolated by filtration, washed with ether (3×15 mL), and dried over sicapent, in vacuo. Yield: 11.23 g (48%). M.p. 112°-119° C. Anal. for C9H12N2O4, found (calc.) C: 51.14 (50.94) H: 5.78 (5.70) N: 11.52 (13.20). The compound showed satisfactory 1H and 13C-NMR spectra.

Workup

  1. temperatureThe solution was refluxed in the dark for 45 h
  2. customevaporated to dryness in vacuo
  3. dissolutionthe residue dissolved in methanol (8 mL)
  4. temperaturewith heating
  5. temperatureAfter cooling in an ice bath
  6. customthe product was precipitated by addition of ether (20 mL)
  7. customisolated by filtration
  8. washwashed with ether (3×15 mL)
  9. customdried over sicapent, in vacuo

Sources & evidence

ORD record
ord-36d52e8af3f44d26aee65f278d810f17
Source dataset
uspto-grants-1998_02
Patent number
US05714331

Reaction notes

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