31408-19-2

Basic information

• Product Name: 5-PHENYL-2-PYRIMIDINETHIOL
• Synonyms: 5-PHENYL-2-PYRIMIDINETHIOL;5-PHENYL-2-PYRIMIDINYLHYDROSULFIDE;5-phenylpyrimidine-2-thiol
• CAS NO: 31408-19-2
• Molecular Formula: C₁₀H₈N₂S
• Molecular Weight: 188.25
• Mol File: 31408-19-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-PHENYL-2-PYRIMIDINETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYL-2-PYRIMIDINETHIOL(31408-19-2)
• EPA Substance Registry System: 5-PHENYL-2-PYRIMIDINETHIOL(31408-19-2)

Safety Data

• Hazardous Substances Data: 31408-19-2(Hazardous Substances Data)

Upstream product

• 53913-71-6 3-chloro-2-phenylpropenal 
• 17356-08-0 thiourea 
• 103-82-2 phenylacetic acid 
• 7089-34-1 ((Z)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate 
• 7089-34-1 ((E)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate 

Downstream Products

• 1609637-39-9 (±)-3,4-dihydro-4,5-diphenylpyrimidine-2(1H)-thione 
• 1609637-40-2 (±)-4-(3-fluorophenyl)-3,4-dihydro-5-phenylpyrimidine-2(1H)-thione 
• 1609637-41-3 (±)-4-(6-methoxypyridin-3-yl)-5-phenyl-3,4-dihydropyrimidine-2(1H)-thione 
• 121743-65-5 2-(3-Butynylthio)-5-phenylpyrimidine 
• 56863-46-8 1-methyl-5-phenyl-2(1H)-pyrimidinone 
• 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 
• 177948-87-7 5-Phenyl-2-trimethylsilanyloxy-pyrimidine 
• 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 
• 177948-95-7 1-[(2S,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-phenyl-1H-pyrimidin-2-one 
• 177948-91-3 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-5-phenyl-2(1H)-pyrimidinone 

Relevant articles and documents

Preparation of 2,5-disubstituted pyrimidines from vinamidinium salts and synthesis of novel disulfane derivatives

Novel pyrimidine derivatives were prepared from the reaction of 2-substituted 1,3-bis(dimethylamino)-trimethinium salts with thiourea or guanidine in the presence of ethyl-diisopropylamine in ethanol at reflux, and also some 5-substituted pyrimidine-2-thi

Regioselective synthesis of novel 4,5-diaryl functionalized 3,4-dihydropyrimidine-2(1H)-thiones via a non-Biginelli-type approach and evaluation of their in vitro anticancer activity

An easy and novel approach to synthesize 4,5-diaryl functionalized 3,4-dihydropyrimidine-2(1H)-thiones via addition of aryllithiums to 5-aryl substituted pyrimidine-2(1H)-thiones, which could be regarded as a method complementary to the most widely used Biginelli-type synthesis, is described. In the reaction of aryllithiums with N-(Me)Bn substituted pyrimidine-2(1H)-thiones a high degree of regioselectivity of addition, leading to 4-aryl adducts, was achieved. Selected compounds tested for their in vitro anticancer activity against four human cancer cell lines showed the greatest activity against breast cancer (MCF7). 1-Benzyl-4-(3-hydroxyphenyl)-5-phenyl substituted 3,4-dihydropyrimidine-2(1H)-thione (10g) exhibiting 10-fold more potent activity than the best known monastrol (MON) stands as a promising candidate for further scaffold and asymmetric synthesis. the Partner Organisations 2014.

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.