59698-21-4

Basic information

• Product Name: 5-Cyclopropyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
• Synonyms: 5-Cyclopropyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
• CAS NO: 59698-21-4
• Molecular Formula: C₇H₈N₂OS
• Molecular Weight: 168.21622
• Mol File: 59698-21-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Cyclopropyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Cyclopropyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one(59698-21-4)
• EPA Substance Registry System: 5-Cyclopropyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one(59698-21-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 59698-21-4(Hazardous Substances Data)

Upstream product

• 17356-08-0 thiourea 
• 34108-21-9 methyl cyclopropylacetate 
• 109-94-4 formic acid ethyl ester 
• 54322-65-5 cyclopropylacetyl chloride 
• 6542-60-5 2-cyclopropylacetonitrile 
• 5239-82-7 cyclopropylacetic acid 
• 72306-36-6 methyl 2-cyclopropyl-3-aldehydeacetate 

Downstream Products

• 59698-20-3 5-cyclopropyl-pyrimidin-2,4-(1H,3H)-dione 
• 108274-18-6 5-cyclopropyl-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythropentofuranosyl]uracil 
• 136160-36-6 5-Cyclopropyl-1-ethoxymethyl-6-phenylsulfanyl-1H-pyrimidine-2,4-dione 
• 136160-37-7 5-Cyclopropyl-1-ethoxymethyl-6-phenylsulfanyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 1190379-86-2 2,4-dichloro-5-cyclopropylpyrimidine 
• 1341200-68-7 2-chloro-4-(3-chloro-4-fluorophenyl)-5-cyclopropylpyrimidine 
• 1341200-44-9 4-(3-chloro-4-fluorophenyl)-5-cyclopropyl-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)pyrimidin-2-amine 
• 1190377-54-8 cyclobutanecarboxylic acid {3-[5-cyclopropyl-2-(3-fluoro-phenylamino)-pyrimidin-4-ylamino]-propyl}-amide 
• 1190377-57-1 thiophene-2-carboxylic acid {3-[5-cyclopropyl-2-(3-fluoro-phenylamino)-pyrimidin-4-ylamino]-propyl}-amide 
• 1190377-92-4 thiophene-2-carboxylic acid {3-[5-cyclopropyl-2-(2-fluoro-phenylamino)-pyrimidin-4-ylamino]-propyl}-amide 
• 1415227-70-1 C₂₂H₂₄FN₅OS 
• 1415227-71-2 C₂₁H₂₉N₅OS 
• 1190377-79-7 cyclobutanecarboxylic acid {3-[5-cyclopropyl-2-(3-morpholin-4-yl-phenylamino)-pyrimidin-4-ylamino]-propyl}-amide 
• 1190378-43-8 cyclobutanecarboxylic acid {3-[5-cyclopropyl-2-(3-1,2,4-triazol-1-ylmethyl-phenylamino)-pyrimidin-4-ylamino]-propyl}-amide 

Relevant articles and documents

As Hedgehog signal transduction pyrimidine amines and pyridine amine inhibitors

The invention relates to pyrimidinamine and pyridinamine Hedgehog signal conduction inhibitors. The inhibitors are compounds with the structure represented by formula (I) or pharmaceutically acceptable salts thereof. The invention also relates to a medicinal use of the above compounds as hedgehog signal conduction inhibitors.

The discovery of novel N-(2-pyrimidinylamino) benzamide derivatives as potent hedgehog signaling pathway inhibitors

Hedgehog signaling pathway inhibitors are emerging as new therapeutic intervention against cancer. A novel series of N-(2-pyrimidinylamino) benzamide derivatives as hedgehog signaling pathway inhibitors were designed and synthesized. Most compounds presented significant inhibitory effect on hedgehog signaling pathway, among which 21 compounds exhibited more potent than vismodegib. Furthermore, compound 6a showed moderate pharmacokinetic properties in vivo, representing a promising lead compound for further exploration.

Free Radical Rearrangements in Uracil Derivatives

As part of an effort to develop general probes for radical reactions involving DNA bases, several uracil derivatives were synthesized.The rates of the cyclopropyl carbinyl rearrangement in these systems were evaluated by means of competition experiments.The results indicate that when a cyclopropyl group is substituted in the 5-position of uracil, the rearrangement occurs very slowly - with a rate constant of -1.On the other hand, the analog of the 5-hexenyl radical cyclization onto the 5,6-double bond of uracil derivatives occurs with rates which were similar to the parent process: (4.0-8.9)E4 s-1.The experimental results along with semiempirical calculations show that radicals 23 and 25 are unusually stable species.These results explain why no rearrangements are observed when a cyclopropyl-substituted thymine dimer is cleaved by reductive single electron transfer.