25855-26-9

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

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

Downstream Products

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

Relevant academic research and scientific papers

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

Palladium-Catalyzed Polyhetero-Claisen Rearrangement of 2-(Allylthio)pyrimidin-4(3H)-ones

The regioselective S -> N allylic transposition of 2-(allylthio)pyrimidin-4(3H)-ones (3) has been performed by catalysis of Pd(II) salts.Generally the rearrangement gives the N-1 alkylation product predominantly over the N-3-alkylation product.Substituents at the 6-position of 3 reverse the selectivity.Both N-1 and N-3 rearrangement products were transformed to thiazolopyrimidones.

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

Copper-Catalyzed Regioselective Direct C–H Thiolation and Thiocyanation of Uracils

A novel copper-catalyzed direct C–H thiolation and thiocyanation of uracils using disulfides and thiocyanate salts respectively as coupling partners are described. These reactions enable the C–H bond cleavage and C–S bond formation to proceed efficiently under relatively mild conditions, providing useful methods for a preparation of a series of thio-substituted at the C5 position of uracil derivatives. These protocols exhibit several merits including simple experimental procedures, readily accessible substrates and reagents, broad scopes, high yields, and excellent regioselectivity. Preliminary mechanistic studies revealed that a radical pathway is likely to be involved.

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.

Design, synthesis, antiviral, and cytostatic evaluation of novel isoxazolidine analogs of homonucleotides

Moderate diastereoselectivities (d.e. 2-62%) of isoxazolidine homonucleotides were observed for cycloadditions between N-methyl-C- (diethoxyphosphoryl)nitrone and N-allyl nucleobases, with trans-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil-containing cycloadducts. The cis- and trans-isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC50 values in the range of 33-100 μM.

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

Microwave-assisted N-allylation of uracil and thymine pyrimidine bases

This work presents a new synthetic approach to N(1)-allylation of pyrimidine nucleobases with allyl bromide. The increased efficiency of the proposed method is based on two specific elements: (a) the nucleoside N-deprotonation is carried out in a homogeneous system by using sodium methylsulfinyl- methylide in DMSO; (b) the allylation reaction is microwave-assisted. This method ensures high yields (87-88%) of the monoallylated products and short reaction time (1.5 h as compared to tens of hours for classical methods), and provides protection against side reactions. NMR analysis of the crude reaction mixture indicated a ratio of 6-8 : 1 between N(1)-allyl derivatives and N(1),N(3)-diallyl derivatives.

Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) were prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, meanwhile the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. A ruthenium-based cross-metathesis reaction was used to synthesize new acycloalkenyl nucleosides.

Synthesis of silicon analogues of acyclonucleotides incorporable in oligonucleotide solid-phase synthesis

The synthesis of the four silicon analogues of acyclonucleosides was described. In every case, the silicon atom was introduced onto an allyl group on the natural nucleobase following a hydrosilylation reaction. Diols obtained were protected as 4,4'-dimethoxytrityl ethers and subsequently activated as 2-cyanoethyl N,N-diisopropylchlorophosphoramidite in order to be suitable for oligonucleotide solid phase synthesis.