II. CHEMISTRY 107 



O 



H / \ 

 X2C— CH CHo (46) X— CH2— C=CH2 (47) 



I 

 X 



o o 



H II II 



X— (oiH)— C— C— CH— OC— CH3 (48) CH2=C— C— H (49) 



I II I I 



X O H(orX) X 



H 

 CHo— CH— CHO + Nal (50, 51) C2H5O— CH2CH— C=0 (52) 



I I I 



X 



I I 



tosyl tosyl 



CI— CH2— C— CH2CI (53) 



II 

 O 



2. COXDEXSATIOX OF PREFORMED PtERIX WITH AROMATIC AmIXE 



These methods involve formation of a 2-amino-4-hydroxy-6-methyl- 

 pteridine with a suitable substituent in the 6-methyl group for reaction with 

 p-aminobenzoic acid. Examples of these are (R = 2-amino-4-hydroxy-6- 

 substituted pteridine) : 



R— CH2CI + p-aminobenzoylglutamic acid (PABG)'*- " 

 R— CHO + PABG in formic acid, followed by hydrolysis*^' " 



■•OI. E. Hultquist and P. F. Dreisbach (to American Cjanamid Co.), U. S. Pat. 



2,472,482 (June 7, 1949). 

 '' J. H. Boothe (to American Cyanamid Co.), U. S. Pat. 2,472,462 (June 7, 1949). 

 " M. E. Hultquist and D. R. Seeger (to American Cyanamid Co.), U. S. Pat. 2,472,481 



(June 7, 1949). 

 " L. Doub and L. Bambas (to Parke, Davis & Co.), U. S. Pat. 2,476,360 (July 19, 



1949). 

 '" P. Karrer and R. Schwyzer, Helv. Chim. Acta 31, 777 (1948). 

 5' P. Karrer (to Hoffman-La Roche, Inc.), U. S. Pat. 2,520,882 (August 29, 1950). 

 " J. Geraci (to American Cyanamid Co.), U. S. Pat. 2,501,168 (March 21, 1950). 

 " D. I. Weisblat and A. R. Hanze (to The Upjohn Company), U. S. Pat. 2,560,616 



(July 17, 1951). 

 " Roche Products, Ltd. Brit. Pat. 624,394 (June 7, 1949). 



"J. H. Boothe (to American Cyanamid Co.), U. S. Pat. 2,547,519 (Apr. 3, 1951). 

 5« Roche Products, Ltd., Brit. Pat. 631,516 (Nov. 3, 1949). 

 " H. Lindhir and H. Khieui (to Hoffmann-La Roche, Inc.), U. S. Pat. 2,520,156 (Aug. 



29, 1950). 



