SYNTHESIS 



6. J. K. Cline, R. R. Williams and J. Finkelstein, ibid., 1052. 



7. E. R. Buchman, R. R. Williams and J. C. Keresztesy, /. Amer. 



Chem. Soc, 1935, 57, 1849. 



8. M. Wohmann, Annalen, 1890, 269, 299. 



9. A. Windaus, R. Tschesche and R. Grewe, Z. physiol. Chem., 1934, 



228, 27. 



10. H. T. Clarke and S. Gurin, /. Amer. Chem. Soc, 1935, 57, 1876. 



11. A. Windaus, R. Tschesche and R. Grewe, Z. physiol. Chem., 1935, 



237, 98. 



12. I.G., B.P. 456735. 



13. R. R. WiUiams, /. Amer. Chem. Soc, 1936, 58, 1063. 



14. R. R. Williams and A. E. Ruehle, ibid., 1935, 57, 1856. 



15. E. R. Buchman, R. R. Williams and J. C. Keresztesy, ibid., 1849. 



/ 



4. SYNTHESIS OF ANEURINE / 



The complete synthesis of aneurine was first announced by R. R. 

 Williams and his co-workers in America, but important contributions 

 were made by A. R. Todd and his collaborators in England, by A. 

 Windaus and his school in Germany, and by K. Makino and T. Imai 

 in Japan. The subject is one of some complexity and papers of 

 fundamental importance appeared within a few weeks or even days 

 of one another, so that it is well-nigh impossible to give a strictly 

 chronological account of the course of events.^ 



The matter is further complicated by the policy of the German 

 workers of withholding publication until patent protection had been 

 adequately effected. Thus H. Horlein ^ states " the priority of the 

 synthesis of the product imdoubtedly rests with Andersag and 

 Westphal ". This may very well be true, for the I.G. began to file 

 patents as early as 1935. Since, however, the paper by H. Andersag 

 and K. Westphal ^ was not published until 1937, over a year after 

 Williams' publication, this belated claim to priority seems rather like 

 an attempt to secure the academic cake as well as the economic half- 

 penny ! 



It will simplify matters if the method of synthesis adopted by each 

 group of workers is discussed in tuxn.^ 



American Method 



R. R. Williams and J. K. Cline ^ condensed ethyl a-formyl-jS- 

 ethoxy-propionate with acetamidine, and converted the resulting 

 5-ethoxymethyl-4-hydroxy-2-methyl-pyrimidine into 4-aniino-5- 

 bromomethyl-2-methyl-pyrimidine by the following series of reactions : 



15 



