503-09-3Relevant articles and documents
PROCESS FOR MANUFACTURING AN EPOXIDE
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Page/Page column 26-30, (2015/07/07)
Process for manufacturing an epoxide by reacting at least one chlorohydrin with at least one dehydrochlorinating agent in order to give the epoxide and at least one chlorinated co-product, said process comprising regenerating the dehydrochlorinating agent from the chlorinated co-product by a treatment which does not comprise an electrolysis operation.
SYNTHESIS OF ISOMERIC N-(3-FLUORO-2-HYDROXYPROPYL) AND N-(2-FLUORO-3-HYDROXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES
Jindrich, Jindrich,Dvorakova, Hana,Holy, Antonin
, p. 1466 - 1482 (2007/10/02)
Reaction of fluoromethyloxirane (III) with heterocyclic bases in the presence of potassium carbonate afforded N-(3-fluoro-2-hydroxypropyl) derivatives of adenine (VI), 3-deazaadenine (VII), 2-amino-6-chloropurine (XII), 6-nitro-1-deazapurine (IX), 4-methoxy-2-pyrimidone (XVIII) and its 5-methyl derivative (XIX).Acid hydrolysis of compounds XII, XVIII, and XIX gave 9-(3-fluoro-2-hydroxypropyl)guanine (XIII), 1-(3-fluoro-2-hydroxypropyl)uracil (XX) and -thymine (XXI).The intermediates XVIII and XIX were ammonolyzed to give 1-(3-fluoro-2-hydroxypropyl)cytosine (XXII) and -5-methylcytosine (XXIII).Reaction of chloro derivative XII with sodium azide followed by hydrogenation of the formed 2-amino-6-azidopurine (XIV) led to 9-(3-fluoro-2-hydroxypropyl)-2,6-diaminopurine (XV), 9-(3-fluoro-2-hydroxypropyl)-1-deazaadenine (X) was obtained by hydrogenation of compound IX.Benzyloxymethyloxirane (XXIV) was reacted with pyridine-hydrogen fluoride adduct to give 3-benzyloxy-2-fluoropropanol (XXV) whose tosylate XXVI on reaction with sodium salt of adenine and subsequent hydrogenolysis of the intermediate XXVII afforded 9-(2-fluoro-3-hydroxypropyl)adenine (XXVIII).The same compound was obtained by reaction of 3-benzoyloxy-1-bromo-2-fluoropropanol (XXX) with sodium salt of adenine followed by methanolysis.Condensation of sodium salt of XI, XVI, and XVII with synthon XXX and subsequent acid deblocking gave 9-(2-fluoro-3-hydroxypropyl)guanine (XXXIII), 1-(2-fluoro-3-hydroxypropyl)uracil (XXXVI), and 1-(2-fluoro-3-hydroxypropyl)thymine (XXXVII). 1-(2-Fluoro-3-hydroxypropyl) derivatives of cytosine (XXXVIII) and 5-methylcytosine (XXXIX) were obtained by ammonolysis of the corresponding 4-methoxypyrimidine intermediates XXXIV and XXXV.
The Combination of Potassium Fluoride and Calcium Fluoride: A Useful Heterogeneous Fluorinating Reagent
Ichihara, Junko,Matsuo, Toshiya,Hanafusa, Terukiyo,Ando, Takashi
, p. 793 - 794 (2007/10/02)
The combination of potassium fluoride and calcium fluoride was found to be an effective and practical solid reagent for the fluorination of various organic chlorides and bromides under mild conditions.