862508-03-0

Basic information

• Product Name: penthyl(5-fluro-2-oxo-1, 2-dihydropyriMidin-4-yl) carbaMate
• Synonyms: penthyl(5-fluro-2-oxo-1, 2-dihydropyriMidin-4-yl) carbaMate;(5-Fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)carbamic acid pentyl ester;Pentyl (5-fluoro-2-oxo-1,2-dihydro-4-pyrimidinyl)carbamate;Pentyl (5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate
• CAS NO: 862508-03-0
• Molecular Formula: C₁₀H₁₄FN₃O₃
• Molecular Weight: 243.2348632
• Mol File: 862508-03-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: penthyl(5-fluro-2-oxo-1, 2-dihydropyriMidin-4-yl) carbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: penthyl(5-fluro-2-oxo-1, 2-dihydropyriMidin-4-yl) carbaMate(862508-03-0)
• EPA Substance Registry System: penthyl(5-fluro-2-oxo-1, 2-dihydropyriMidin-4-yl) carbaMate(862508-03-0)

Safety Data

• Hazardous Substances Data: 862508-03-0(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Pentyl(5-fluro-2-oxo-1,2-dihydropyriMidin-4-yl) carbaMate is used as a fungicide for the control of plant pathogens. It serves as an effective agent in protecting crops from various fungal infections, ensuring better crop yield and quality.
As a derivative of fluorocytosine, penthyl(5-fluro-2-oxo-1,2-dihydropyriMidin-4-yl) carbaMate leverages the antimicrobial properties of its parent compound, making it a valuable asset in the agricultural sector for managing plant diseases and maintaining a healthy growing environment.

InChI:InChI=1S/C10H14FN3O3/c1-2-3-4-5-17-10(16)14-8-7(11)6-12-9(15)13-8/h6H,2-5H2,1H3,(H2,12,13,14,15,16)

Upstream product

• 638-41-5 pentyl chloroformate 
• 2341-22-2 5-fluorocytidine 
• 2022-85-7 Flucytosine 

Downstream Products

• 162204-20-8 N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine 
• 154361-50-9 capecitabine 

Relevant articles and documents

Preparation method of capecitabine impurity (5-fluoro-2-oxo-1,2-dihydropyrimidine-4-yl)amylcarbamate

The invention discloses a preparation method of a capecitabine impurity (5-fluoro-2-oxo-1,2-dihydropyrimidine-4-yl)amylcarbamate. According to the method, 5-flucytosine and n-amyl chloroformate reactin an organic solvent to produce (5-fluoro-2-oxo-1,2-dihydropyrimidine-4-yl)amylcarbamate with pyridine as an acid binding agent and tetrabutylammonium bromide as a phase transfer catalyst. The preparation method comprises simple steps, the yield (90% or higher) is high, and the prepared product has higher purity (99% or higher) and can be completely used as an impurity reference substance to be used for quality research of capecitabine.

A capecitabine key intermediate synthesis method

The invention discloses a synthetic method for capecitabine key intermediate 2`,3`-O-diacetylpyridine-5`-deoxygenation-5-fluorine-N4-[(pentyloxy) carbonyl] cytidine. The synthetic method for the capecitabine key intermediate comprises the following steps that 1, 5- fluorocytosine, an acid-binding agent, chloroform, water and phase transfer catalyst are mixed, pentyl chloroformate is added dropwise under stirring, and the chloroform solution of (5-fluorine-2-oxo-1,2-dihydropyrimidine-4-base) amylcarbamate is obtained; 2, 1,2,3-three-O-acetyl-5-deoxygenation-6- ribofuranose is added into the chloroform solution obtained in the step 1, lewis acid is added dropwise, the reaction is performed for 2-10 hours after adding, and the capecitabine key intermediate is obtained after post-processing. The synthetic method is simple and convenient in operation, a silicane protective agent and intermediate product purification are not needed, the high yield of finished products is achieved, the proportion of alpha isomer in the products is effectively controlled, and compared with literature data, the purity of the obtained products is greatly improved.

Capecitabine preparation method

The invention discloses a capecitabine preparation method; 5-FU as a raw material is subjected to a reaction with pentyloxy formyl chloride, then an intermediate is generated and then is coupled with a ribose derivative, an ethoxyl protective group of ethoxyl of the ribose derivative is removed in the coupling reaction, and thus the target compound capecitabine is obtained; the method comprises the following steps: step one, the 5-FU as the raw material is subjected to the reaction with pentyloxy formyl chloride, and then the intermediate is generated; and step two, the intermediate is coupled with the ribose derivative to generate the product capecitabine. The production cost can be saved, the medical expense of patients is reduced, the side effect is reduced, and the yield is higher.

Rapid continuous synthesis of 5′-deoxyribonucleosides in flow via Br?nsted acid catalyzed glycosylation

A general, green, and efficient Br?nsted acid-catalyzed glycosylation serves as a key step in the one-flow, multistep syntheses of several important 5′-deoxyribonucleoside pharmaceuticals.

METHOD FOR THE PREPARATION OF CAPECITABINE AND INTERMEDIATES USED IN SAID METHOD

A process to obtain capecitabine compound and its pharmaceutically acceptable derivatives is hereby disclosed. Likewise, novel intermediates to be used in the preparation of capecitabine compound and its pharmaceutically acceptable derivatives are also disclosed. The procedure comprises the stage of causing a reaction of N4-(n-pentyloxycarbonyl))-5- fluorocytosine with (1,2,3-tri-O-acetyl-5-deoxy- α,β-D-ribofuranose.

PROCESS FOR PREPARING CAPECITABINE

There is provided processes for the preparation of capecitabine and intermediates thereof.

5'-deoxy-n-(substituted oxycarbonyl)-5-fluorocytosine and derivatives thereof, method of preparing same, and anticancer composition comprising same as active ingredients

Disclosed is a new fluorocystosine and derivatives thereof. The fluorocystosine and derivatives thereof provide a pharmaceutical composition exhibiting better anti-cancer characteristics than the conventional composition.