55779-18-5

Usage

Uses

Used in Veterinary Medicine:
Arprinocide is used as a coccidiostat for the prevention and treatment of coccidiosis in poultry. It is effective against various species of Eimeria, which are responsible for causing this disease. By controlling the growth and proliferation of these parasites, Arprinocide helps maintain the health and productivity of the birds.

Originator

Arprinocid,NANJING PHARMA

Manufacturing Process

To a solution of potassium t-butoxide in absolute ethanol slowly adding dry adenine. This mixture was stirred for about 2 h, and then 2-chloro-6- fluorobenzyl chloride was added over a period of about 4 h. The resulting mixture was heated to reflux with stirring and allowed to react for about 42 h, after which it was cooled to about 10°C. The crude product thus formed was isolated by filtration and then washed with ice cold ethanol and ice cold water to yield a 6-amino-9-(2-chloro-6-fluorobenzyl)purine.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 960, 1978 DOI: 10.1021/jo00399a034

InChI:InChI=1/C12H9ClFN5/c13-8-2-1-3-9(14)7(8)4-19-6-18-10-11(15)16-5-17-12(10)19/h1-3,5-6H,4H2,(H2,15,16,17)

Upstream product

• 55117-15-2 2-chloro-6 fluorobenzyl chloride 
• 66224-66-6 adenine 
• 40428-86-2 sodium adeninate 

Downstream Products

• 76099-79-1 9-(2-chloro-6-fluorobenzyl)-6-diethylaminopurine 
• 70091-23-5 9-(2-chloro-6-fluorobenzyl)-6-dimethylaminopurine 
• 76099-77-9 9-(2-chloro-6-fluorobenzyl)-1-methyladenine hydroiodide 
• 72564-77-3 9-(2-chloro-6-fluorobenzyl)purin-6(1H)-one 
• 70091-21-3 9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine 
• 72564-76-2 6-chloro-9-(2-chloro-6-fluorobenzyl) purine 
• 76099-76-8 9-(2-chloro-6-fluorobenzyl)-6-anilinopurine 
• 72564-81-9 9-(2-chloro-6-fluorobenzyl)-6-butylaminopurine 
• 76099-82-6 9-(2-chloro-6-fluorobenzyl)-6-iso-butylaminopurine 
• 72564-87-5 9-(2-chloro-6-fluorobenzyl)-6-benzylaminopurine 
• 76099-84-8 9-(2-chloro-6-fluorobenzyl)-6-pentylaminopurine 
• 76099-81-5 9-(2-chloro-6-fluorobenzyl)-6-dipropylaminopurine 
• 76099-80-4 9-(2-chloro-6-fluorobenzyl)-6-isopropylaminopurine 
• 76099-83-7 9-(2-chloro-6-fluorobenzyl)-6-sec-butylaminopurine 

Relevant academic research and scientific papers

Preparation method for high-purity 9-[(2-chloro-6-fluorophenyl)methyl]-9H-purine-6-amine

The invention discloses a preparation method for high-purity 9-[(2-chloro-6-fluorophenyl)methyl]-9H-purine-6-amine, and belongs to the technical field of chemical synthesis. The preparation method comprises the following steps: (1) adenine salt preparation: in a reactor, adding adenine, water and strong base, stirring for dissolved clarification, carrying out reduced pressure distillation to remove solvent, and obtaining an adenine salt crude product; (2) in a reactor full of the adenine salt crude product, adding amide polar solvent to be fully dissolved, cooling, adding 2-chloro-6-fluorobenzoyl chloride to react, and after reaction ends, carrying out reduced pressure distillation to remove the amide polar solvent to obtain a 9-[(2-chloro-6-fluorophenyl)methyl]-9H-purine-6-amine crude product; carrying out recrystallization to obtain a fine product. The preparation process is a homogeneous phase system, a reaction condition is mild, and yield is high; catalyst is not required, and a raw materials technology is simple; the prepared target product has the advantages of high content, high purity and low byproduct content.

Process for formulating a synthetic drug for use in animal feed, and resulting formulation

A method of formulating a synthetic drug for use in animal feed, for the purpose of reducing carry-over of the synthetic drug to subsequent lots of animal feed in the feed mill.

Production of purine derivatives and intermediates therefor

Improved processes for producing purine derivatives, such as 9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine, which are useful as anticoccidial agents, and new arylazopyrimidine compounds of the formula: STR1 wherein R1 and R2 each is hydrogen, C1-3 alkyl, allyl or dihalobenzyl, and when either one of R1 and R2 is hydrogen, the other is other than hydrogen, and R3 is aryl, and acid addition salts thereof, which are useful as intermediates for production of the purine derivatives.

Phase-Transfer Catalysis in the N-Benzylation of Adenine

A convenient phase-transfer catalysis in the N-benzylation of adenine is described.The benzylation of adenine with benzyl halides in a two-phase system containing phase-transfer catalyst gave 9-benzylated adenines as a major product accompanied with 3-benzylated adenines.

Process for purification of 9-(2,6-dihalobenzyl)adenines

An efficient method has been found for the removal of the 3-isomer present in crude 9-(2-chloro-6-fluorobenzyl)adenine. Crude 9-(2-chloro-6-fluorobenzyl)adenine is transalkylated in sulfuric acid-toluene to reduce the 3-isomer to undetectable levels (100 ppm). Alternately, crude 9-(3-chloro-6-fluorobenzyl)adenine is first treated with dilute nitric acid to remove the bulk of the 3-isomer followed by transalkylation to sulfuric acid-toluene to reduce the 3-isomer to undetectable levels (100 ppm). The overall yield for this purification is about 95% based on the 9-(2-chloro-6-fluorobenzyl)adenine content of the crude material. The resulting pure 9-(2-chloro-6-fluorobenzyl)adenine has anticoccidial activity and is useful in controlling cecal and/or intestinal coccidiosis when administered in minor quantities to animals, in particular to poultry usually in admixture with animal sustenance.

Process for preparation of 9-(dihalobenzyl) adenines

9-(Dihalobenzyl)adenines are prepared uncontaminated with other positional isomers in a series of mild transformations starting from 4,5,6-triaminopyrimidine and proceeding via 7-(N-formyl-N-dihalobenzyl)amino[1,2,5]thiadiazolo[3,4-d]pyrimidine. The resulting compounds have anticoccidial activity and are useful in controlling cecal and/or intestinal coccidiosis when administered in minor quantities to animals, in particular to poultry usually in admixture with animal sustenance.

Process for preparation of 9-(2,6-dihalobenzyl)adenines

9-(2,6-Dihalobenzyl)adenines are prepared by allowing 2,6-dihalobenzyl halides to react with a salt of adenine in a solid-liquid or liquid-liquid two phase system in the presence of an onium salt phase transfer catalyst. The resulting compounds have anticoccidial activity and are useful in controlling cecal and/or intestinal coccidiosis when administered in minor quantities to animals, in particular to poultry usually in admixture with animal sustenance.