154121-06-9

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione,5-fluorodihydro-6-methoxy-,cis-(9CI)
• Synonyms: 2,4(1H,3H)-Pyrimidinedione,5-fluorodihydro-6-methoxy-,cis-(9CI)
• CAS NO: 154121-06-9
• Molecular Formula: C5H7FN2O3
• Molecular Weight: 162.12
• Product Categories: HALIDE
• Mol File: 154121-06-9.mol

Chemical Properties

• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• PKA: 8.40±0.60(Predicted)
• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione,5-fluorodihydro-6-methoxy-,cis-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione,5-fluorodihydro-6-methoxy-,cis-(9CI)(154121-06-9)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione,5-fluorodihydro-6-methoxy-,cis-(9CI)(154121-06-9)

Safety Data

• Hazardous Substances Data: 154121-06-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 51-21-8 5-fluorouracil 
• 56311-36-5 cis-5-fluoro-6-acetoxy-5,6-dihydrouracil 
• 56311-36-5 6-Acetoxy-5-fluoro-5,6-dihydrouracil 
• 66-22-8 uracil 

Relevant articles and documents

Photochemical reactions of 5-fluoropyrimidine bases with alcohols

Photochemical reactions of 5-fluorocytosine with primary alcohols led to 5-alkoxycytosines and 6-alkoxycytosines as the main photoproducts. These products are formed via reactive intermediates 6-alkoxy-5-fluoro-5,6- dihydrocytosines, whereas photochemical reactions of 5-fluorouracil with alcohols led to stable 6-alkoxy-5-fluoro-5,6-dihydrouracils.

Fluorinated Pyrimidines. Part 4. Synthesis, Properties and Stereochemical Conversion of the cis and trans Isomers of 6-Alkoxy-5-fluoro-5,6-dihydrouracils

The reaction of 6-acetoxy-5-fluoro-5,6-dihydrouracil with ROH (R=Me, Et, Pr, Pri, Bu, But) under acidic conditions has been investigated using 18F as a tracer.The quantitative replacement of the OAc-group proceeded predominantly with cisoid (gauche) stereochemistry, but upon prolonged heating the amount of the trans compound increased.This isomerization did not originate from epimerization at C5.The trans compounds-apart from being more stable towards substitution and elimination than the corresponding cis compounds-gave invariably substitution products with inversion of configuration, while the cis compounds mainly retained their configuration.Within the concept of the unifying ion-pair mechanism it is proposed that the trans compound reacts via an intimate protonated intermediate and the cis compound via a solvent-separated protonated intermediate.As a result, it was not the gauche attraction between the fluorine atom and the incoming nucleophile, but the poor ?-donor ability of the C-F bond that was the determining factor in the cisoid stereochemistry of 5-fluoro-5,6-dihydrouracil adducts.

Process for preparation of 6-substituted 5-fluorouracil derivatives

The reaction of certain fluorinated pyrimidine derivatives with hydrogen donor compounds to produce 6-substituted 5-fluoropyrimidines is disclosed. The products so produced are useful in germicidal and antineoplastic applications, and can be converted into 5-fluorouracil, which has known utility in cancer chemotherapy.