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Ethyl-5-fluoro-pyrimidin-2-yl-amine, also known as FPAA, is a chemical compound that is commonly used as a building block in the production of various pharmaceuticals, agrochemicals, and other chemical products.
As a versatile intermediate, FPAA can be transformed into a variety of downstream products through a range of chemical reactions and synthesis methods.
Upstream Products
The production of FPAA begins with the synthesis of 2-fluoro-5-nitro-pyrimidine, which is then transformed into 2-fluoro-5-nitro-4H-pyrimidin-4-one through a nitration reaction.
This intermediate is then reduced to 2-fluoro-5-aminopyrimidine-4-carboxylic acid by a reductive nitrilation process, and finally, the acid is esterified with ethyl bromide to produce Ethyl-5-fluoro-pyrimidin-2-yl-amine.
Downstream Products
- Pharmaceuticals
FPAA is a common precursor in the production of various pharmaceuticals, including anti-inflammatory drugs, antibiotics, and antivirals.
For example, FPAA can be transformed into the active ingredient of the common pain reliever Naproxen, which is used to treat pain, fever, and inflammation.
FPAA can also be converted into the anti-tuberculosis drug Rifampicin, and the anti-HIV drug Stavudine. - Agrochemicals
FPAA is used as an intermediate in the production of agrochemicals, such as herbicides and pesticides.
It can be transformed into the active ingredient of the herbicide Atrazine, which is widely used to control weeds in agricultural fields.
FPAA can also be converted into the insecticide Chlorpyrifos, which is used to control pests in crops. - Other Chemical Products
FPAA can also be used as a building block in the production of other chemical products, such as dyes, catalysts, and polymers.
For example, FPAA can be transformed into the intermediate for the production of the dye Methyl Orange, which is used in textile and leather industries.
Processes
There are several processes for converting FPAA into downstream products, depending on the desired product and the specific reaction conditions.
Some of the common chemical reactions and synthesis methods include:
- Nitration: The conversion of 2-fluoro-5-nitro-pyrimidine to 2-fluoro-5-nitro-4H-pyrimidin-4-one, which is then reduced to 2-fluoro-5-aminopyrimidine-4-carboxylic acid.
- Esterification: The conversion of 2-fluoro-5-aminopyrimidine-4-carboxylic acid into Ethyl-5-fluoro-pyrimidin-2-yl-amine through an esterification reaction with ethyl bromide.
- Reductive nitrilation: The conversion of 2-fluoro-5-nitro-4H-pyrimidin-4-one to 2-fluoro-5-aminopyrimidine-4-carboxylic acid through a reductive nitrilation process.
- Condensation: The conversion of FPAA into the active ingredient of pharmaceuticals and agrochemicals through condensation reactions, such as the synthesis of Naproxen and Atrazine.
Challenges and Opportunities
The production of FPAA and its downstream products is a complex process that requires strict control of reaction conditions and the use of specialized equipment.
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