25855-26-9

Basic information

• Product Name: 1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE
• Synonyms: 1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE
• CAS NO: 25855-26-9
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• Mol File: 25855-26-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 109 °C(Solv: ethanol (64-17-5))
• Appearance: /
• Density: 1.179g/cm³
• Refractive Index: 1.515
• PKA: 9.67±0.10(Predicted)
• CAS DataBase Reference: 1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE(25855-26-9)
• EPA Substance Registry System: 1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE(25855-26-9)

Safety Data

• Hazardous Substances Data: 25855-26-9(Hazardous Substances Data)

Usage

Appearance

Yellow crystalline powder

Potential applications

Pharmaceuticals and agrochemicals

Chemical class

Pyrimidinediones

Structural feature

Contains an allyl group

Reactivity

Versatile building block for synthesis of various compounds

Functionalization

Ability to undergo various functionalization reactions

Importance

Important intermediate in production of biologically active compounds

Current status

Actively explored in development of new drugs and agrochemical products

InChI:InChI=1/C7H8N2O2/c1-2-4-9-5-3-6(10)8-7(9)11/h2-3,5H,1,4H2,(H,8,10,11)

Upstream product

• 6204-00-8 1-allyl-2-methylsulfanyl-1H-pyrimidin-4-one 
• 94731-99-4 1-Allyl-4-methylsulfanyl-1H-pyrimidin-2-one 
• 591-87-7 Allyl acetate 
• 66-22-8 uracil 
• 134692-47-0 (Z)-4-(benzyloxy)-2-butenyl acetate 
• 89693-81-2 1-allyl-2-thioxo-2,3-dihydro-pyrimidin-4(1H)-one 
• 66-22-8 4-Hydroxy-1H-pyrimidin-2-one 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 762-72-1 allyl-trimethyl-silane 
• 106-95-6 allyl bromide 
• 365515-75-9 N¹-allyl-N³-benzoyluracil 
• 31170-22-6 2-Allylsulfanyl-1H-pyrimidin-4-one 

Downstream Products

• 130967-33-8 (E)-3-Methyl-1-(3-trityloxypropyl-1-enyl)uracil 
• 130967-34-9 (Z)-3-Methyl-1-(3-trityloxypropyl-1-enyl)uracil 
• 130967-32-7 3-Methyl-1-(2-methylsulphonyloxy-3-trityloxypropyl)uracil 
• 130967-31-6 1-(2-Hydroxy-3-trityloxypropyl)-3-methyluracil 
• 191086-95-0 N-[1-(3-{[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-hydroxymethyl-methyl-silanyl}-propyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 191086-92-7 N-{1-[3-(Bis-hydroxymethyl-methyl-silanyl)-propyl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 

Relevant articles and documents

A new route to acyclic nucleosides via palladium-mediated allylic alkylation and cross-metathesis

A method for the syntheses of E-unsaturated acyclic nucleosides via a combination of palladium-catalyzed allylic alkylation and ruthenium-based cross metathesis is described. This approach provides a concise, efficient and reliable route to new nucleoside

Regioselective synthesis of 1-allyl- and 1-arylmethyl uracil and thymine derivatives

2,4-Bis(trimethylsiloxy) pyrimidines 1 with allyl halides and arylmethyl halides in 1,2-dichloroethane in the presence of I2 regioselectively provide 1-allyl-/1-arylmethyl-uracil and thymine derivatives. The secondary aryl alkyl and diaryl meth

The Convenient Synthesis of Unsaturated Nucleoside Analogues in Water under Microwave Irradiation

A convenient method for the regioselective synthesis of unsaturated nucleoside analogs in water under microwave irradiation was developed. All pyrimidine and purine nucleoside derivatives were exclusively alkylated at N1 and N9 respectively in good to excellent yields. In addition, this system could tolerate a broad range of functional groups, such as chloro, bromo, iodo, alkyl, amino, and hydroxyl groups. More importantly, the reaction scale could be enlarged to 50 mmol which made this route attractive for industrial application.

A new route to N1-substituted uracil derivatives using hypervalent iodine

In continuation of our previous study, oxidative coupling reactions of uracil with allylsilane or enol ethers were examined using diacetoxyiodobenzene. The reaction of persilylated uracil with 3,4-dihydro-2H-pyran in the presence of TMSOTf and PhI(OAc)res