36327-91-0

Basic information

• Product Name: 6-FORMYL-URACIL MONOHYDRATE
• Synonyms: 4-FORMYLURACIL MONOHYDRATE;6-URACILCARBOXALDEHYDE;6-FORMYL-URACIL MONOHYDRATE;OROTALALDEHYDE;RARECHEM AH CK 0107;6-FORMYL-URACIL MONOHYDRATE 98%;6-FORMYL-URACIL MONOHYDRATE >98%;4-Pyrimidinecarboxaldehyde, 1,2,3,6-tetrahydro-2,6-dioxo- (6CI,9CI)
• CAS NO: 36327-91-0
• Molecular Formula: C₅H₄N₂O₃
• Molecular Weight: 158.11
• Product Categories: PYRIMIDINE
• Mol File: 36327-91-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 340℃ (dec.)
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: /
• Density: 1.567±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.86E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 5.63±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 6-FORMYL-URACIL MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FORMYL-URACIL MONOHYDRATE(36327-91-0)
• EPA Substance Registry System: 6-FORMYL-URACIL MONOHYDRATE(36327-91-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 36327-91-0(Hazardous Substances Data)

Usage

Uses

Uracil-6-carboxaldehyde monohydrate is used as pharmaceutical intermediates.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 4, p. 163, 1967 DOI: 10.1002/jhet.5570040138

InChI:InChI=1/C5H4N2O3.H2O/c8-2-3-1-4(9)7-5(10)6-3;/h1-2H,(H2,6,7,9,10);1H2

Upstream product

• 16953-49-4 6-diethoxymethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 16953-48-3 6-diethoxymethyl-1H-pyrimidine-2,4-dione 
• 626-48-2 6-Methyluracil 

Downstream Products

• 22126-44-9 6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione 
• 65-86-1 orotic acid 
• 183204-74-2 Tipiracil 
• 73742-45-7 5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione 

Relevant articles and documents

-

-

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.

Preparation method of tipiracil intermediate

The invention provides a preparation method of a tipiracil intermediate which is 6-(chloromethyl)-2, 4-(1H, 3H)-pyrimidinedione. 6-methyl-2, 4-(1H, 3H)-pyrimidinedione as an initial raw material undergoes an iodine replacement reaction at the 5th site of a compound and then the product undergoes reduction and chlorination reactions at the 6th site to produce a desired product. The preparation method has the advantages of stable processes, high yield and low cost and is suitable for industrial production.

Fragment-based approach to the design of 5-chlorouracil-linked-pyrazolo[1, 5-a][1,3,5]triazines as thymidine phosphorylase inhibitors

5-Chlorouracil-linked-pyrazolo[1,5-a][1,3,5]triazines were designed as new thymidine phosphorylase inhibitors based on the fragment based drug design approach. Multiple-step convergent synthetic schemes were devised to generate the target compounds. The intermediate 5-chloro-6-chloromethyluracil was synthesized by a 4-step reaction. A series of the second bicyclic intermediates, namely pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-one, was obtained from various substituted 3-aminopyrazoles. These two intermediates were coupled finally in the presence of sodium ethoxide and methanol to yield the desirable target compounds. The methylthio coupling spacer was found to be suitable in enabling the interaction of the two fragments at the active site and allosteric site of the enzyme. The best coupled compound (9q) inhibited the thymidine phosphorylase with an IC50 value as low as 0.36 ± 0.1 μM. In addition, 9q demonstrated a mixed-type of enzyme inhibition kinetics, thus suggesting that it might indeed potentially bind at two different sites on the enzyme. Georg Thieme Verlag KG Stuttgart New York ISSN 0935-8943.