21473-22-3

Upstream product

• 402849-08-5 3-benzyl-1-t-butoxycarbonylthymine 
• 100-44-7 benzyl chloride 
• 65-71-4 thymin 
• 538-32-9 benzylurea 
• 144410-12-8 5-Methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 25902-91-4 2-methoxy-5-methylpyrimidin-4(3H)-one 
• 402848-98-0 tert-butyl 5-methyl-2,4-dioxo-1,2,3,4-tetrahydro pyrimidine-1-carboxylate 
• 100-39-0 benzyl bromide 
• 696617-65-9 1-benzhydryl-5-methyl-1H-pyrimidine-2,4-dione 
• 821795-57-7 1-benzhydryl-3-benzylthymine 
• 253142-26-6 3-benzyl-2-methoxy-5-methyl-4-pyrimidinone 
• 199444-45-6 3-Benzyl-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 78450-19-8 dibenzyl-1,3 thymine 
• 82387-34-6 (E)-3-(3-Benzyl-ureido)-2-methyl-acrylic acid methyl ester 

Downstream Products

• 186387-59-7 3-benzyl-1-(3-chloro-propyl)-5-methyl-1H-pyrimidine-2,4-dione 
• 284042-73-5 3-benzoyl-5-methyl-1-vinylpyrimidine-2,4(1H, 3H)-dione 
• 4330-20-5 N-3-benzoylthymine 
• 592527-82-7 3-benzyl-5-methyl-1-(3-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-yl}-propyl)-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis of (Carbo)nucleoside analogues by [3+2] annulation of aminocyclopropanes

(Carbo)nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine-, uracil-, and 5-fluorouracil-substituted diester donor-acceptor cyclopropanes and their use in the indium- and tin-catalyzed [3+2] annulations with aldehydes, ketones, and enol ethers. The obtained diester products could be easily decarboxylated and reduced to the corresponding alcohols. The method gives access to a broad range of new (carbo)nucleoside analogues in only four or five steps and will be highly useful for the synthesis of libraries of bioactive compounds.

Deprotection of N-BOC compounds

Organic compounds having nitrogen atoms protected with t-butoxycarbonyl are effectively deprotected by heating in a fluorinated alcohol solution.

Deprotection of N-BOC compounds

Organic compounds having nitrogen atoms protected with t-butoxycarbonyl are effectively deprotected by heating in a fluorinated alcohol solution.

Novel practical deprotection of N-Boc compounds using fluorinated alcohols

The thermolytic deprotection of N-Boc compounds was accomplished using TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) as solvents. Even though the cleavage of the t-butylcarbamate (Boc) group can be achieved at solvent reflux temperature, the deprotection process was significantly accelerated under microwave-assisted conditions. The practicality of this methodology was demonstrated on alkyl, aryl, and heteroaromatic N-Boc-amines. Copyright Taylor & Francis Group, LLC.

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

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.

SYNTHESIS OF METHYL 3-(N'-ALKYLUREIDO)-2-METHYL-2-PROPENOATES AND THEIR CYCLIZATION TO 3-ALKYL-5-METHYLURACILS

Stereoisomeric methyl 3-(N'-alkylureido)-2-methyl-2-propenoates (Ia-Id) were prepared by acid-catalyzed reaction of N-alkylureas (R = methyl, benzyl, isopropyl and tert-butyl) with methyl 3-methoxy-2-methyl-2-propenoate (III).Reaction of the ester III with N-tert-butylthiourea afforded the thioureides (E)-Ie and (Z)-Ie.On treatment with sodium methoxide in methanol, compounds Ia-Ic cyclized to the corresponding 3-alkyl-5-methyluracils IIa-IIc whereas compounds Id and Ie underwent only a base catalyzed E/Z isomerization with (E)-isomers predominating.