Process for producing 8-fluoropurines
AssigneeThe Regents of the University of California
InventorsJorge R. Barrio, Nagichettiar Satyamurthy, Mohammad Namavari, Michael E. Phelps
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Abstract
An efficient, regiocontrolled approach to the synthesis of 8-fluoropurines by direct fluorination of purines with dilute elemental fluorine, or acetyl hypofluorite, is provided. In a preferred embodiment, a purine compound is dissolved in a polar solvent and reacted with a dilute mixture of F.sub.2 in He or other inert gas.
Claims13
A method of making an 8-fluoropurine compound, comprising:
- introducing elemental fluorine or acetyl hypofluorite into a solution containing a purine compound.
A method of making an 8-fluoropurine compound of the formula ##STR4## where X and Y independently are alkyl, aryl, arylalkyl, alkoxy, aryloxy, acetyl, amino, substituted amino, protected amino, carbamoyl, alkoxyamino, aryloxyamino, alkylcarbonylamino, alkoxyacetylamino, aryloxyacetylaiio, benzoylamino, tritylamino, halogen, hydroxy, or hydrogen;
- R is alkyl, aryl, arylalkyl, hydrogen, ribofuranosyl, protected ribofuranosyl, deoxyribofuranosyl, dideoxyribofuranosyl, hydroxyalkoxy lower alkyl, or protected hydroxyalkoxy lower alkyl,
- and each alkyl or aryl moiety independently is unsubstituted or substituted with one or more of hydroxy, halogen, lower alkyl or lower alkoxy, comprising;
- reacting, in a polar solvent, a purine compound of the formula ##STR5## where X, Y and R are as recited above, with elemental fluorine or acetyl hypofluorite mixed with an inert gas.
A method for making an 8-fluoropurine compound, comprising:
- replacing hydrogen with fluorine at the C(8) position of a purine compound by reacting the purine compound with elemental fluorine (F.sub.2) or acetyl hypofluorite.
Dependencies are inferred from the claim text.