CHEMISTRY: JOHNSON AND HADLEY 
419 
We have now continued our investigation on the hydrolysis of pyri- 
midine-nucleosides and have examined the behavior towards acids of 
the ethyl ether of the corresponding secondary nucleoside of thymine 
III. This pyrimidine has already been synthesized and a description 
of the properties of the compound is given in a dissertation presented by 
Dr. Hadley in 1916.2 ^ow find that this pyrimidine III interacts 
in a manner perfectly analogous to that shown by its lower homologue 
I. When heated under pressure with an aqueous solution of hydro- 
chloric acid it is transformed as expected into the nucleoside IV with 
evolution of ethyl chloride. On continued heating, however, the nu- 
cleoside IV gradually breaks down with evolution of carbon dioxide, and 
is changed into a compound of unknown structure having the formula 
C6H10ON2. The transformation is expressed by the following equation. 
NH— CO 
CO C CH3 
NH— CO 
CO C CH3 
C6H10ON2 + CO2 
OC2H5 
NH— CCHCH3 
III. 
OH 
NH— C CH CH3 
IV. 
In other words, the two hydrolytic products C5H8ON2 and C6H10ON2 
are combinations of the same order and are representatives of an homolo- 
gous series differing in constitution by a CH2 radical. 
The compound C6H10ON2 derived from the nucleoside ether III has 
a melting or decomposition point of 270°. We have subjected the com- 
bination to a complete analysis and have obtained the following ana- 
lytical results. Carbon 56.88%, hydrogen 8.10% and nitrogen 21.96%. 
The theoretical values for these three elements respectively in a com- 
pound having the formula C6H10ON2 are carbon 57.1%, hydrogen 7.9% 
and nitrogen 22.2%. 
Our observation that pyrimidines of the type represented by formulas 
II and IV readily loose one of their carbon atoms is unique in that the 
change can be brought about by simple hydrolysis and without the 
employment of an oxydizing agent. The mother compounds from which 
the nucleosides are derived viz. : uracil and thymine, can be heated with 
acids at high temperatures for hours without destruction of the pyri- 
midine ring. The final results of our investigation will be pubHshed in 
the Journal of the American Chemical Society. 
^Johnson and Hadley, /. Amer. Chem. Soc, Easlon, Fa., 38, 1916, (1844). 
2 Hadley, Sidney E., Dissertation, Yale University, 1916. 
