56863-46-8

Upstream product

• 57-13-6 urea 
• 4432-64-8 hydroxymethylenephenylacetaldehyde 
• 31408-19-2 2-mercapto-5-phenylpyrimidine 
• 26591-66-2 2-phenyl-1,3-propanedial 

Downstream Products

• 177948-87-7 5-Phenyl-2-trimethylsilanyloxy-pyrimidine 
• 22536-62-5 2-chloro-5-phenypyrimidine 
• 177949-08-5 Benzoic acid (2R,3S,4R,5R)-4-acetoxy-3-methanesulfonyloxy-5-(2-oxo-5-phenyl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 177948-96-8 Methanesulfonic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2-oxo-5-phenyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 177948-94-6 1-((2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-phenyl-1H-pyrimidin-2-one 
• 177948-93-5 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-phenyl-1H-pyrimidin-2-one 
• 178035-69-3 Benzoic acid (2S,5S)-5-(2-oxo-5-phenyl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 177949-22-3 Benzoic acid (2S,5R)-5-(2-oxo-5-phenyl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 

Relevant academic research and scientific papers

Addition of C-nucleophiles to 5-phenylpyrimidin-2(1H)-ones and 6-phenyl-1,2,4-triazin-3(2H)-one

Addition reactions of C-nucleophiles to the C=N bond of 5-phenyl- and 1-methyl-5-phenylpyrimidin-2(1H)-ones 1a,b and 6-phenyl-1,2,4-triazin-3(2H)-one 2 were investigated. 1a,b and 2 furnished addition products with indoles; 1a also added N-methylpyrrole. Only 2 added thiophene and methyl ketones, and reacted with alkyl halides and acetone forming products resulting both from alkylation and from addition of acetone at positions 2 and 5, respectively.

PYRIMIDIN-2-ONE COMPOUNDS AND THEIR USE AS DOPAMINE D3 RECEPTOR LIGANDS

The invention relates to pyrimidin-2-one compounds of general formula (I), in addition to the derivatives and tautomers of (I) and the physiologically acceptable salts of said compounds. In said formula: A represents linear or branched C3-C6 alkene, which can have a double bond or triple bond and/or a group Z, which is not adjacent to the nitrogen atom of the pyrimidinone ring and is selected from O, S, C(O), NR3, C(O)NR3, NR3C(O), OC(O) and C(O)O; B represents a group of formula (II), in which X stands for CH2 or N and Y stands for CH2 or CH2CH2, or X-Y can also jointly represent C=CH, C=CH-CH2 or CH-CH=CH; R1 and R 2 are defined as cited in the description and the claims; and Ar represents an optionally substituted aromatic group. The invention also relates to a pharmaceutical agent, containing at least one compound (I) and the tautomers, derivatives and/or acid addition salts of said compound, optionally together with physiologically acceptable carriers and/or auxiliary agents. The invention also relates to the use of compounds of formula (I), and their tautomers, derivatives and pharmacologically acceptable acid addition salts for producing a pharmaceutical agent for treating diseases, which respond to the influence of dopamine D3 receptor ligands.

Synthesis of 5-phenyl-2(1H)-pyrimidinone nucleosides

Reaction of 2-phenyltrimethinium salt 1 with thiourea and subsequent reaction with chloroacetic acid afforded 5-phenyl-2(1H)-pyrimidinone (3). Its silyl derivative 4 was condensed with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose under catalysis with tin tetrachloride or trimethylsilyl trifluoromethanesulfonate to give protected nucleoside 5 together with 5′,O 6-cyclo-5-phenyl-1,3-bis-(β-D-ribofuranosyl)-6-hydroxy-5,6- dihydro-2(1H,3H)-pyrimidinone (7). The greatest amounts of 7 were formed with the latter catalyst. Nucleosidation of the silyl derivative 4 with protected methyl 2-deoxy-D-ribofuranoside 8 or 2-deoxy-D-ribofuranosyl chloride 9 afforded 1-(2-deoxy-3,5-di-O-p-to-luoyl-β-D-ribofuranosyl)-5-phenyl-2(1H)- pyrimidinone (10) and its α-anomer 11. Reaction of 10 and 11 with methanolic ammonia gave free 2′-deoxynucleosides 12 and 13. Compound 13 was converted into 5′-O-tert-butyldiphenylsilyl-3′-O-mesyl derivative 14 which on heating with 1,8-diazabicydo[5.4.0]undec-7-ene (DBU) and subsequent cleavage with tetrabutylammonium fluoride afforded 2′,3′-dideoxy-2′,3′-didehydronucleoside 15. Reaction of the silyl derivative 4 with 1,2-di-O-acetyl-3,5-di-O-benzoylxylofuranose (18), catalyzed with tin tetrachloride, furnished 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-xylofuranosyl)-2(1H)-pyrimidinone (19) which was deprotected to give the β-D-xylofuranosyl derivative 22. As a side product, the nucleosidation afforded the β-D-xylopyranosyl derivative 23. Deacetylation of compound 19 gave 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)-5-phenyl-2(1H)-pyrimidinone (24) which on reaction with thionyl chloride afforded 2′-chloro-2′-deoxynucleoside 25 and 2′,O6-cyclonucleoside 26. Heating of compound 25 with DBU in dimethylformamide furnished the lyxo-epoxide 27 which on reaction with methanolic ammonia was converted into free 1-(2,3-anhydro-β-D-lyxofuranosyl)-5-phenyl-2(1H)-pyrimidinone (28). Reaction of 1,2-di-O-acetyl-5-O-benzoyl-3-O-methanesulfonyl-D-xylofuranose (30) with silyl derivative 4 gave the nucleoside 31 which by treatment with DBU was converted into an equilibrium mixture of 5′-benzoylated arabinofuranoside 33a and its 2′,6-anhydro derivative 33b.