Synthesis of 1-Substituted 5-Aminoimidazole-4-carbaldehydes and 8-Amino-1-(2-fluorobenzyl)imidazo[4’,5’:5,6]pyrido[2,3-d]pyrimidine

Abstract

The syntheses of a number of 1-substituted 5-aminoimidazole-4-carbaldehydes 3, by the reduction of the corresponding 5-amino-4-cyanoimidazole derivatives is reported using LiAlH(OEt)₃, prepared in situ from LiAlH₄ and ethyl acetate. The compounds of type 1 are useful intermediates for the synthesis of elongated adenine derivatives.

Key words

heterocycles - imidazoles - cyanides - aldehydes - imidazo[4’,5’:5,6]pyrido[2,3-d]pyrimidines

References

• 1a Stephen H. J. Chem. Soc.  1925,  1874 
• 1b Stephen H. J. Chem. Soc.  1930,  2786 
• 2a Reiman E. Liebigs Ann. Chem.  1978,  1963 
• 2b Weistock LT. O’Brien DE. Cheng CC. J. Med. Chem.  1968,  11:  1238 
• 2c Taurins A. Khnouw VT. Can. J. Chem.  1973,  51:  1741 
• 3a Bredereck H. Simchen G. Traut H. Chem. Ber.  1967,  100:  366 
• 3b Tieckelmann H. Guthrie R. Nairn JG. J. Org. Chem.  1960,  25:  1257 
• 3c Arpad G. Odon F. Oszkár F. Magy. Kem. Foly.  1955,  61:  112 
• 4 Perandones F. Soto JL. J. Heterocycl. Chem.  1997,  34:  107 
• 5 Alves MJ. Booth BL. Al-Duaij OKh. Eastwood P. Nezhat L. Proença MFJRP. Ramos AS. J. Chem. Res. (M)  1993,  2701 
• 6 Butula I. Liebigs Ann. Chem.  1969,  729:  73 
• 7 Brown HC. Garg CP. J. Am. Chem. Soc.  1964,  86:  1085 
• 8a Kelley JL. Krochmal MP. Linn JA. McLean EW. Soroko FE. J. Med. Chem.  1988,  31:  606 
• 8b Kelley JL. Krochmal MP. Linn JA. McLean EW. Soroko FE. J. Med. Chem.  1988,  31:  1005 
• 9 Al-Shaar AHM. Chambers RK. Gilmour DW. Lythgoe DJ. McClenaghan I. Ramsden CA. J. Chem. Soc., Perkin Trans. 1  1992,  2789 
• 10 Harris PA. Pendergast W. J. Heterocycl. Chem.  1996,  33:  319 
• 11 Booth BL. Costa FAT. Mahmood Z. Pritchard RG. Proença MFJRP. J. Chem. Soc., Perkin Trans. 1  1999,  1853 
• 12 Gilmore CJ. J. Appl. Crystallogr.  1984,  17:  42 

13

Beurskens, P. T. DIRDIF: Direct Methods for Difference Structures - An Automatic Procedure for Phase Extension and Refinement of Difference Structure Factors, Technical report 1984/1, Crystallography Laboratory: Toernooiveld, 6525 Ed, Nijmegen, 1984.