40338-28-1

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione,1-acetyl-
• Synonyms: Uracil,1-acetyl- (6CI,7CI); 1-Acetyluracil; NSC 266142
• CAS NO: 40338-28-1
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.1234
• Mol File: 40338-28-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.387g/cm³
• Refractive Index: 1.532
• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione,1-acetyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione,1-acetyl-(40338-28-1)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione,1-acetyl-(40338-28-1)

Safety Data

• Hazardous Substances Data: 40338-28-1(Hazardous Substances Data)

Usage

General Description

The chemical 2,4(1H,3H)-Pyrimidinedione,1-acetyl- is a compound with the molecular formula C6H6N2O3. It is a derivative of pyrimidinedione and is also known as 6-Acetyluracil. 2,4(1H,3H)-Pyrimidinedione,1-acetyl- is commonly used as a pharmaceutical intermediate and in the synthesis of various pharmaceutical compounds. It has potential applications in the development of antiviral and antitumor drugs. Additionally, 2,4(1H,3H)-Pyrimidinedione,1-acetyl- can also be used as a building block in organic synthesis and chemical research.

InChI:InChI=1/C6H6N2O3/c1-4(9)8-3-2-5(10)7-6(8)11/h2-3H,1H3,(H,7,10,11)

Upstream product

• 66-22-8 uracil 
• 108-24-7 acetic anhydride 

Downstream Products

• 5236-64-6 (2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetic acid butyl ester 
• 1820-81-1 5-chlorouracil 
• 696-07-1 5-iodouracil 
• 14383-43-8 2-(2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)acetic acid 

Relevant articles and documents

Synthesis and carbonic anhydrase inhibitory properties of novel uracil derivatives

Abstract Carbonic anhydrase (CA) inhibitors are valuable molecules based on several therapeutic applications, including antiglaucoma activity. In the present study, inhibition of two human cytosolic carbonic anhydrase isozymes I and II with some uracil derivatives (3-9) were investigated. Compounds 3-9 showed KI values in the range of 10.83-464 μM for hCA I and of 28.88-778.5 μM against hCA II, respectively. Kinetic investigations showed that similarly to classical CA inhibitors, all investigated natural compounds act as competitive inhibitors with 4-NPA as substrate. Uracil derivatives investigated here are promising agents which may be used as lead molecules in order to derivative novel carbonic anhydrase inhibitors that might be useful in medical applications.

Unexpected Reaction Products of Uracil and Its Methyl Derivatives with Acetic Anhydride and Methylene Chloride

New acetyl derivatives of uracil, 6-methyluracil, and thymine were obtained in the course of an unconventional synthesis in methylene chloride. It was shown that products with the acetyloxymethyl fragment are formed according to a mechanism different from that for products with the acetyloxyethyl group. In particular, for uracil it was proven that the reaction with Ac2O, TEA, and CH2Cl2 leads to 1-acetyloxymethyluracil, where the N1 substituent is composed of the -CH2- fragment that originated from CH2Cl2 and the 1-acetyloxy moiety from Ac2O. The reaction of uracil with Ac2O, TEA, CH2Cl2, and DMAP leads to an acetyloxyethyl derivative in which the -CH2-CH2- fragment originates from TEA and the 1-acetyloxy moiety from Ac2O. A possible mechanism for the formation of new compounds was suggested and supported by the density functional theory/B3LYP quantum mechanical calculations. New compounds (39 in total, including seven deuterated) were fully characterized by nuclear magnetic resonance and high-resolution mass spectrometry techniques.

IODO- AND CHLORODEMERCURATION OF 5,5'-MERCURIBISURACILS

The direct C mercuration in the 5 position of 1-acetyluracil by means of mercury(II) trifluoroacetate in anhydrous acetonitrile is described.The intermediately formed 1-acetyl-5-trifluoroacetoxymercuriuracil, without isolation, was subjected to symmetrization by the action of potassium iodide.The acetyl groups were then readily split out by the action of water.The resulting 5,5'-mercuribisuracil (50percent yield) forms 5-iodo- or 5-chlorouracil in 93percent or 72percent yields, respectively, under the influence of an aqueous KI3 solution or excess pure liquid S2Cl2.