ChemicalBook CAS DataBase List 6-(HYDROXYMETHYL)URACIL

6-(HYDROXYMETHYL)URACIL synthesis

8synthesis methods

Product Name:6-(HYDROXYMETHYL)URACIL
CAS Number:22126-44-9
Molecular formula:C5H6N2O3
Molecular Weight:142.11

36327-91-0
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22126-44-9
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Yield:22126-44-9 98%

Reaction Conditions:

with sodium tetrahydroborate in methanol; for 4 h;Reflux;

Steps:

Preparation of model compound

The synthesis of 6-HOMU includes two steps (Fig. 2): synthe-sis of orotaldehyde and reduction of orotaldehyde to 6-HOMU. Theorotaldehyde was prepared by Kwang-Yuen’s method [23]. Briefly,6-methyl uracil (2.54 g) was refluxed in acetic acid (60 mL) withselenium dioxide (2.66 g) for 6 h. The hot reaction mixture was fil-tered and the yellow filtrate collected and solvent evaporated. Thecrude orotaldehyde was then dissolved in hot water (24 mL) and5% sodium bisulfite was added dropwise into the stirred mixture.The solution was boiled with active carbon for 10 min and thengravity filtered to remove the carbon. The filtrate was acidified to pH 1 using concentrated HCl. Upon cooling, pure orotaldehyde wasobtained as a precipitate from the solution. A mixture of pure oro-taldehyde (0.14 g) and sodium borohydride (0.076 g) was refluxedin 95% methanol for 4 h. The resulting solution was filtered and thesolvent was evaporated yielding the pure 6-HOMU with the purityof 98%.

References:

Zhao, Cen;Pelaez, Miguel;Dionysiou, Dionysios D.;Pillai, Suresh C.;Byrne, John A.;O'Shea, Kevin E. [Catalysis Today,2014,vol. 224,p. 70 - 76]

6153-44-2 Synthesis