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Nelarabine is a synthetic compound that is widely used in the pharmaceutical industry for the treatment of cancer.
It is a nucleoside analogue that is specifically used for the treatment of T-cell lymphoma, a type of blood cancer that affects the immune system.
The synthetic route of nelarabine is a complex and multistep process that involves the synthesis of several intermediate compounds.
In this article, we will discuss the synthetic routes of nelarabine in detail.
Step 1: The synthesis of 2,6-diaminopurine
The synthesis of nelarabine begins with the synthesis of 2,6-diaminopurine, which is an intermediate compound in the production of nelarabine.
This compound can be synthesized through several different routes, including the N-Boc saltylization of 2,6-diaminopyridine, the N-Boc aldol condensation of ethyl 3-dimethylaminopropionate, and the Suzuki reaction of 2-((S)-2-(diplopterylamino)indan-1-yl)acetic acid with boronic acid.
Step 2: The synthesis of 5-oxoprolinyl ovaride
The next step in the synthesis of nelarabine is the synthesis of 5-oxoprolinyl ovaride, which is another intermediate compound.
This compound can be synthesized through several different routes, including the Williamson ether synthesis of 4-methoxy-2-oxopropanamide, the Prenzel reaction of 3-methyl-2-oxo-1,2-oxazolidine-4-carboxylic acid with 2-chloromethyl-3-oxo-1,2,3,4-tetrahydro-pyrrole-1-ium iodide, and the anti-Claisen condensation of 2-chloromethyl-3-oxo-1,2,3,4-tetrahydro-pyrrole-1-ium iodide with 5-formyl-2-oxoprolinamide.
Step 3: The synthesis of N-hydroxy-2,2-dimethyl-4-oxo-1,3,2,4-tetrahydro-pirimidine-5-amide
The synthesis of N-hydroxy-2,2-dimethyl-4-oxo-1,3,2,4-tetrahydro-pirimidine-5-amide is the next step in the synthesis of nelarabine.
This compound can be synthesized through several different routes, including the Pechmann condensation of 2,2-dimethyl-4-oxo-1,3,2,4-tetrahydro-pirimidine-5-amide with benzaldehyde, the Bischler-Napieralski reaction of 2-chloromethyl-5-hydroxymethyl-2,3-oxazepanone with 2-hydroxy-2,3-dimethyl-4-oxo-1,3,2,4-tetrahydro-pirimidine, and the reduction of 2,2-dimethyl-4-oxo-1,3,2,4-tetrahydro-pirimidine-5-carbaldehyde with lithium aluminum hydride.
Step 4: The synthesis of 2-chloromethyl-3-oxo-1,2,3,4-tetrahydro-p yrrole-1-ium iodide
The synthesis of 2-chloromethyl-3-oxo-1,2,3,4-tetrahydro-p yrrole-1-ium iodide is the next step in the synthesis of nelarabine.
This compound can be synthesized through several different routes, including the Swern oxidation of 3-hydroxy-2-butanone, the halogenation of 3-methyl-2-oxo-1,2,3,4-tetrahydro-p yrrole with bromine, and the halogenation of 3-methyl-2-oxo-1,2,3,4-tetrahydro-