Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1998-04-01
1999-11-30
Berch, Mark L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
C07D47340, C07B 3900
Patent
active
059945419
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase under 35 U.S.C. .sctn.371 of prior PCT International Application No., PCT/JP97/02617, which has an International filing date of Jul. 28, 1997, which designated the United States of America, the entire contents of which are hereby incorporated by reference.
TECHNICAL FIELD
The present invention relates to a process for preparing 2-amino-6-iodopurine. More particularly, the present invention relates to a process for preparing 2-amino-6-iodopurine, which is useful as an intermediate of antiviral agents, and the like.
BACKGROUND ART
Conventionally, 2-amino-6-iodopurine has been prepared by a method comprising reacting 2-amino-6-chloropurine with aqueous hydriodic acid at -10.degree. C. (J. Pharm. Sci. 1968, 57(12), 2056-2061).
However, in this method, it is necessary to use 12 mol of expensive hydriodic acid per 1 mol of 2-amino-6-chloropurine. Also, because the yield of the resulting 2-amino-6-iodopurine is as low as about 25%, the method is not being industrially advantageous.
An object of the present invention is to provide a process for simply, industrially and advantageously preparing 2-amino-6-iodopurine.
DISCLOSURE OF INVENTION
According to the present invention, there can be provided a process for preparing 2-amino-6-iodopurine comprising the steps of suspending at least one chloropurine compound selected from 2-formylamino-6-chloropurine, 2-formylamino-6-chloropurine acetate and 2-amino-6-chloropurine in a solution comprising aqueous hydriodic acid and an alkyl ketone having 3 to 7 carbon atoms; and stirring the resulting suspension at 0.degree. to 50.degree. C.
BEST MODE FOR CARRYING OUT THE INVENTION
In the present invention, one of the features resides in the use of a solution comprising aqueous hydriodic acid and an alkyl ketone having 3 to 7 carbon atoms.
In the present invention, the amount of the expensive hydriodic acid can be remarkably decreased by using the above solution. Further, the desired 2-amino-6-iodopurine can be obtained at high yield of about 90%.
The chloropurine compound, a starting raw material which can be used in the present invention, is at least one member selected from 2-formylamino-6-chloropurine, 2-formylamino-6-chloropurine acetate and 2-amino-6-chloropurine as described above. The 2-formylamino-6-chloropurine, 2-formylamino-6-chloropurine acetate and 2-amino-6-chloropurine can be used alone or in admixture.
The 2-formylamino-6-chloropurine can be prepared according to conventional methods, for example, by a method disclosed in Japanese Patent Laid-Open No. Hei 6-157530.
The 2-formylamino-6-chloropurine acetate can be prepared according to conventional methods, for example, by a method disclosed in Japanese Patent Laid-Open No. Hei 6-157530.
The 2-amino-6-chloropurine is a commercially available compound. The 2-amino-6-chloropurine can be prepared according to conventional methods, for example, by a method disclosed in J. Pharm. Sci. 1968, 57(12), 2056-2061.
The aqueous hydriodic acid used in the present invention can be obtained by dissolving hydriodic acid in water. The concentration of hydriodic acid in the aqueous hydriodic acid is not particularly limited. It is desired that the concentration of hydriodic acid in the aqueous hydriodic acid is usually 30 to 60% by weight or so. The aqueous hydriodic acid is commercially available.
It is desired that the amount of the aqueous hydriodic acid is usually such that the amount of hydriodic acid is adjusted to 1 to 10 mol, preferably 4 to 5 mol, per 1 mol of the chloropurine compound.
Concrete examples of the alkyl ketone having 3 to 7 carbon atoms include, for example, acetone, methyl ethyl ketone, diethyl ketone, methyl isopropyl ketone, diisopropyl ketone, and the like. Among them, acetone is preferable. The alkyl ketone is a commercially available compound.
It is desired that the amount of the alkyl ketone is from 10 to 500 parts by weight, preferably from 20 to 100 parts by weight, more preferably from 40 to 70 parts by weight, still more preferably from 40 to 60 part
REFERENCES:
patent: 3132144 (1964-05-01), Hitchings et al.
patent: 5608064 (1997-03-01), Singh et al.
Koda, J. Pharm. Sci. 57, 2056, 1968.
Bisacchi, J. Org. Chem 60, 2902, 1995.
R.T. Koda et al., "Synthesis of Some Iodopurine Derivatives, Journal of Pharmaceutical Sciences," pp. 2056-2061.
Abstract for JP 06-206879 (Jul. 1994).
Hayashi Taketo
Kuwata Masaaki
Nishiwaki Kenji
Berch Mark L.
Sumika Fine Chemicals Co., Ltd.
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