Pemetrexed Intermediate
This compound, diethyl N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamate 4-methylbenzenesulfonate (CAS 165049-28-5), is an advanced protected precursor of the antifolate anticancer drug pemetrexed disodium, sometimes designated pemetrexed intermediate INT-5. It is a solid that must be stored in the dark under inert atmosphere at room temperature because the pyrrolopyrimidinone core is sensitive to light, moisture and oxidation, and it is catalogued as a pharmaceutical intermediate rather than a finished active substance. The molecule already contains the complete carbon skeleton of the active ingredient, with the two glutamic acid carboxyl groups masked as ethyl esters, while the tosylate salt provides crystallinity, purity control and easy handling. Final ester hydrolysis furnishes pemetrexed.
1. Anticancer drug manufacture: used as a penultimate intermediate in the commercial synthesis of pemetrexed disodium, a multitargeted antifolate thymidylate synthase inhibitor approved for malignant pleural mesothelioma and non-small-cell lung cancer.
2. Synthetic strategy value: the diethyl ester and tosylate salt protect the glutamic acid moiety during construction of the pyrrolopyrimidine ring system and are removed in a final hydrolysis step that generates the active diacid.
3. Analytical and regulatory importance: a critical quality-control point in pemetrexed process development with defined specifications for assay, chiral purity, related substances and residual solvents, and a key material in drug master file documentation.
4. Handling and storage: light, air and moisture sensitive; keep in the dark under inert gas at room temperature, use anhydrous conditions during manipulation, protect personnel from dust exposure and dispose of waste as regulated pharmaceutical chemical waste.
Product Name: Pemetrexed Intermediate
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