1-[(4-Amino-2-propyl-5-pyrimidinyl)methyl]-2-picolinium chloride, Amprovine, Amprolium, Amprol, Anticoccid
3D model (JSmol)
|C14H19N4+ · Cl−|
|Molar mass||278.780 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses in poultry farming
Coccidia are protozoans that can wreak havoc in a flock of poultry by an infection known as coccidiosis. Agents that control this disease–coccidiostats–are in view of the world's heavy dependence on poultry as a source of protein, of great economical significance.
Condensation of ethoxymethylenemalononitrile (1) with acetamidine (2) affords the substituted pyrimidine (4). The rxn may well involve conjugate addition of the amidine nitrogen to the malononitrile followed by loss of ethoxide (3); addition of the remaining amidine nitrogen to one of the nitriles will then lead to the pyrimidine (4). Reduction of the nitrile gives the corresponding aminomethyl compound (5). Exhaustive methylation of the amine followed by displacement of the activated quaternary nitrogen by bromide ion affords the key intermediate (7). Displacement of the halogen by α-picoline gives amprolium.
- Shinkichi Shimizu, Nanao Watanabe, Toshiaki Kataoka, Takayuki Shoji, Nobuyuki Abe, Sinji Morishita, Hisao Ichimura (2000). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.
- Grewe, R. Z. Physiol. Chem. (1936).
- "Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-30.
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