183204-74-2

Basic information

• Product Name: 5-Chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1H,3H)-dione,
• Synonyms: 5-Chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1H,3H)-dione,;5-Chloro-6-[(2-imino-1-pyrrolidinyl)methyl]-2,4(1H,3H)-pyrimidinedione;MA 1 (pharmaceutical);TPI (thymidine phosphorylase inhibitor)
• CAS NO: 183204-74-2
• Molecular Formula: C9H11ClN4O2
• Molecular Weight: 242.66224
• EINECS: -0
• Mol File: 183204-74-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.71±0.1 g/cm3(Predicted)
• PKA: 7.06±0.10(Predicted)
• CAS DataBase Reference: 5-Chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1H,3H)-dione,(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1H,3H)-dione,(183204-74-2)
• EPA Substance Registry System: 5-Chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1H,3H)-dione,(183204-74-2)

Safety Data

• Hazardous Substances Data: 183204-74-2(Hazardous Substances Data)

Usage

Description

5-Chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1H,3H)-dione is a member of the class of pyrimidones, specifically a derivative of uracil with chloro and (2-iminopyrrolidin-1-yl)methyl groups substituted at positions 5 and 6, respectively. It is a compound with potential applications in the pharmaceutical industry due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
5-Chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1H,3H)-dione is used as an active pharmaceutical ingredient for the treatment of advanced or relapsed unresectable colorectal cancer. It is administered in combination with trifluridine, a nucleoside metabolic inhibitor, to enhance the therapeutic effects and improve patient outcomes.
The compound's application in the treatment of colorectal cancer is based on its ability to target and inhibit specific cellular processes involved in cancer cell growth and proliferation. By combining it with trifluridine, the overall effectiveness of the treatment is increased, providing a more comprehensive approach to managing this type of cancer.

Upstream product

• 73742-45-7 5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione 
• 7544-75-4 2-iminopyrrolidine-hydrochloride 
• 91447-90-4 methyl 5-chloro-2,6-dioxo-3H-pyrimidine-4-carboxylate 
• 6153-44-2 methyl orotate 
• 872-34-4 2-imino-pyrrolidine 
• 18592-13-7 6-chloromethyluracil 
• 2101241-71-6 5-chloro-6-(2-oxopyrrolidin-1-yl)methyl-2,4-(1H,3H)pyrimidinedione 
• 36327-91-0 orotoaldehyde 
• 626-48-2 6-Methyluracil 

Relevant articles and documents

Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 2: Optimization of inhibitors of human thymidine phosphorylase and their selectivity with uridine phosphorylase

A series of novel 6-methylene-bridged uracil derivatives have been optimized for clinical use as the inhibitors of human thymidine phosphorylase (TP). We describe their synthesis and evaluation. Introduction of a guanidino or an amidino group enhanced the in vitro inhibitory activity of TP comparing with formerly reported inhibitor 1. Their selectivity for TP based on uridine phosphorylase inhibitory activity was also evaluated. Compound 2 (TPI) has been selected for clinical evaluation based on its strong TP inhibition and excellent modulation of 2′-deoxy-5-(trifluoromethyl)uridine (F3dThd) pharmacokinetics. As a result, TAS-102 (a combination of F3dThd and TPI) is currently in phase 1 clinical studies.

SOLID STATE FORMS OF 5-CHLORO-6-[(2-IMINOPYRROLIDIN-1-YL)METHYL]PYRIMIDINE-2,4-(1H,3H)-DIONE HYDROCHLORIDE AND THEIR PROCESSES FOR THE PREPARATION THEREOF

The present invention relates to solid state forms of 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione hydrochloride compound of formula-1a and their processes for the preparation thereof and an improved process for the preparation of 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione hydrochloride. The present inventors also provides an amorphous polymorph of the combination drug consisting of 2'-deoxy-5-(trifluoromethyl) uridine and 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione monohydrochloride and its process for the preparation.

5 - Chloro -6 - [(2 - imino -1 - pyrrolidine) methyl] - 2, 4 (1 H, 3 H) - dione or its salt preparation method

The invention provides a preparation method of 5-chloro-6-[(2-imino-1-pyrrolidinyl)methyl]-2,4(1H,3H)-pyrimidine dione or salts thereof, which comprises the following steps: by using 6-methylpyrimidyl-2,4(1H,3H)-dione as an initial raw material, carrying out 6- site methyl oxidation and 5- site hydrogen chlorination, reducing the 6- site formyl group, carrying out condensation with 2-aminopyrrolidine or corresponding salts to obtain the target product. The method is simple to operate and stable in technique, is suitable for industrial production, and has the advantages of high yield, high purity and low cost.