126215-85-8

Basic information

• Product Name: 5-Chloro-2-(pent-4-yn-1-yl)pyriMidine
• Synonyms: 5-Chloro-2-(pent-4-yn-1-yl)pyriMidine
• CAS NO: 126215-85-8
• Molecular Formula: C9H9ClN2
• Molecular Weight: 180.63416
• Mol File: 126215-85-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-Chloro-2-(pent-4-yn-1-yl)pyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-(pent-4-yn-1-yl)pyriMidine(126215-85-8)
• EPA Substance Registry System: 5-Chloro-2-(pent-4-yn-1-yl)pyriMidine(126215-85-8)

Safety Data

• Hazardous Substances Data: 126215-85-8(Hazardous Substances Data)

Upstream product

• 88499-78-9 chlorhydrate d'hexyn-5-yl amidine 
• 14918-21-9 5-hexynonitrile 

Downstream Products

• 126215-93-8 3-chloro-6,7-dihydro-5H-1-pyrindine 
• 1386997-94-9 [3-((R)-5-amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-(3-chloro-6,7-dihydro-5H-[1]pyrindin-7-yl)-amine 
• 1386998-16-8 (R)-5-[5-((RS)-3-chloro-6,7-dihydro-5H-[1]pyrindin-7-ylamino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one 
• 1386998-17-9 (R)-5-[5-((RS)-3-chloro-6,7-dihydro-5H-[1]pyrindin-7-ylamino)-2-fluoro-phenyl]-5-methyl-morpholin-3-thione 
• 108994-73-6 6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile 

Relevant articles and documents

Intramolecular inverse electron-demand [4+2] cycloadditions of ynamidyl-tethered pyrimidines: Comparative studies in trifluorotoluene and sulfolane

Three representative 6,7-dihydro-5H-cyclopenta[b]pyridin-4-amines were synthesized using an intramolecular inverse electron demand hetero–Diels–Alder/retro–Diels–Alder sequence between pyrimidines (acting as azadienes) and ynamides (acting as dienophiles). Two solvents of this reaction, sulfolane and trifluorotoluene, were compared at 210 °C and the former consistently led to higher yields. In addition, these studies confirmed the importance of the steric bulk of the C5-position of the pyrimidinyl cycloaddition precursor.

INTRAMOLECULAR DIELS-ALDER REACTIONS OF 2-(ALKYNYL)PYRIMIDINES AND 2-(ALKYNYL)PYRIDINES

Pyrimidines 3,7 and 13 carrying an ο-alkynyl side-chain -CR2(CH2)nCH2CCH (R=H, CN; n=1,2) at the 2-position undergo intramolecular inverse electron demand Diels-Alder reactions across the C-2 and C-5 positions.Loss of hydrogen cyanide, caused by a retro-Diels-Alder reaction, from the intermediate cycloadducts leads to annelated pyridines 5,9 and 15, respectively.Similarly, from the nitropyridines 16 the 2,3-dihydronitro-1H-indenes 18 are obtained.The influence of electronic and steric effects on the rate of cycloaddition is discussed.Gem-disubstitution on the chain connecting the reaction centers leads to a considerable rate enhancement for compounds 3 vs 13.Compounds 7, having an extra methylene group in the tether between diene and dienophile, react much slower than compounds 3 due to decreased entropic assistance.