28734-85-2

Upstream product

• 113094-26-1 3-benzyl-5,8-methano-3,4,r-4a,c-5,c-8,c-8a-hexahydroquinazoline-2,4-dione 
• 6146-23-2 3-benzylpyrimidine-4(3H)-one 
• 34001-56-4 1,3-dibenzyluracil 
• 100-39-0 benzyl bromide 
• 402848-96-8 tert-butyl 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-carboxylate 
• 538-32-9 benzylurea 
• 122-51-0 orthoformic acid triethyl ester 
• 162513-77-1 N-benzylcarbamoyl-4-phenylsulfonylazetidin-2-one 
• 113094-22-7 (1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzylamide 
• 402848-97-9 3-benzyl-2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-carboxylic acid tert-butyl ester 
• 253142-23-3 3-benzyl-2-methoxy-4-pyrimidinone 

Downstream Products

• 20406-84-2 1-methyl-3-(phenylmethyl)pyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Studies toward the oxidative and reductive activation of C-S bonds in 2′-S-aryl-2′-thiouridine derivatives

Studies directed toward the oxidative and reductive desulfurization of readily available 2′-S-aryl-2′-thiouridine derivatives were investigated with the prospect to functionalize the C2′-position of nucleosides. The oxidative desulfurization-difluorination strategy was successful on 2-(arylthio)alkanoate surrogates, while extension of the combination of oxidants and fluoride sources was not an efficient fluorination protocol when applied to 2′-S-aryl-2′-thiouridine derivatives, resulting mainly in C5-halogenation of the pyrimidine ring and C2′-monofluorination without desulfurization. Cyclic voltammetry of 2′-arylsulfonyl-2′-deoxyuridines and their 2′-fluorinated analogues showed that cleavage of the arylsulfone moiety could occur, although at relatively high cathodic potentials. While reductive-desulfonylation of 2′-arylsulfonyl-2′-deoxyuridines with organic electron donors (OEDs) gave predominantly base-induced furan type products, chemical (OED) and electrochemical reductive-desulfonylation of the α-fluorosulfone derivatives yielded the 2′-deoxy-2′-fluorouridine and 2′,3′-didehydro-2′,3′-dideoxy-2′-fluorouridine derivatives. These results provided good evidence of the generation of a C2′-anion through carbon-sulfur bond cleavage, opening new horizons for the reductive-functionalization approaches in nucleosides.

The efficiency of C-4 substituents in activating the β-lactam scaffold towards serine proteases and hydroxide ion

The presence of a leaving group at C-4 of monobactams is usually considered to be a requirement for mechanism-based inhibition of human leukocyte elastase by these acylating agents. We report that second-order rate constants for the alkaline hydrolysis an

Benzhydryl as an efficient selective nitrogen protecting group for uracils

Regioselective N-substitution of the less active nitrogen within uracil analogues has been achieved following preliminary N-protection at the more active N-position with a benzhydryl protecting group. This protecting group is stable to concentrated HCl (a

Ammonium formate/palladium on carbon: A versatile system for catalytic hydrogen transfer reductions of carbon-carbon double bonds

Various carbon-carbon double bonds in olefins and α,β -unsaturated ketones were effectively reduced to the corresponding alkanes and saturated ketones, using ammonium formate as a hydrogen transfer agent in the presence of Pd/C as catalyst in refluxing methanol.

Solid-phase synthesis of 4(1H)-quinolone and pyrimidine derivatives based on a new scaffold - Polymer-bound cyclic malonic acid ester

An efficient method for the preparation of polymer-bound cyclic malonic acid ester starting from Merrifield resin has been developed. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequent double substitution with

N-3-alkylation of uracil and derivatives via N-1-BOC protection

An easy and efficient synthesis of 3-alkyluracils is described. Thus, BOC-protection at N-1 of uracil permits selective alkylation at N-3. This protecting group can be removed under very mild conditions.

HSAB driven chemoselectivity in alkylation of uracil derivatives. A high yielding preparation of 3-alkylated and unsymmetrically 1,3-dialkylated uracils

A qualitative hardness scale (N134) has been found for the conjugated bases of 2-methoxy-4(3H)-pyrimidinones 1-3 and applied to high yielding chemoselective N3 methylation, ethylation and benzylation reactions. Removal of the 2-methoxy group followed by a second alkylation affords unsymmetrically 1,3-disubstituted uracils.

Direct N3 Alkylation of Uracil and Derivatives via N1-[2-(trimethylsilyl)ethoxymethyl] Protection

Protection at N1 position of uracil and uracil analogs as 2-(trimethylsilyl)ethoxymethyl derivatives permits the clean alkylation at N3. These protected uracils are quite stable in a wide range of pH.

A useful methodology for the regioselective deprotection of 1,3-dibenzyluracils

A practical, regioselective N-1 deprotection of 1,3-dibenzyl uracils 2 a-e is described. The same experimental procedure and longer reaction time afforded the complete deprotection of the uracils.