77373-45-6

Basic information

• Product Name: 2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine
• Synonyms: [1]benzothieno[2,3-d]pyrimidin-4-amine, 5,6,7,8-tetrahydro-2-methyl-
• CAS NO: 77373-45-6
• Molecular Formula: C₁₁H₁₃N₃S
• Molecular Weight: 219.306
• Mol File: 77373-45-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 347°C at 760 mmHg
• Flash Point: 163.6°C
• Density: 1.33g/cm³
• Vapor Pressure: 5.55E-05mmHg at 25°C
• Refractive Index: 1.711
• CAS DataBase Reference: 2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine(77373-45-6)
• EPA Substance Registry System: 2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine(77373-45-6)

Safety Data

• Hazardous Substances Data: 77373-45-6(Hazardous Substances Data)

Upstream product

• 4651-91-6 3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene 
• 75-05-8 acetonitrile 
• 77287-34-4 formamide 
• 108-94-1 cyclohexanone 
• 89567-04-4 2-chloromethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl-amine 

Relevant articles and documents

Synthesis and DNase I inhibitory properties of some 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines

A series of six novel and six known thieno[2,3-d]pyrimidin-4-amines 2–13 were synthesized, and further were used as a starting material for preparation of a small series of eight novel thieno[2,3-d]pyrimidin-4-phthalimides 14–21. Eight compounds, five amine and three phthalimide derivatives, inhibited bovine pancreatic DNase I with an IC50 below 200 μM, being more effective than referent inhibitor crystal violet. Phthalimide derivatives 16, 18 and 19 exhibited higher DNase I inhibitory activity compared to their amine precursors 7, 10 and 11. Compound 19, as the most potent (IC50 = 106 ± 16 μM), offers a good starting point for a design of new DNase I inhibitors. The Pharma RQSAR model showed a significant enhancement of thieno[2,3-d]pyrimidines activity using aryl substituents at R1 position. The E-State RQSAR model clarified the most important structural fragments relevant for DNase I inhibition. Molecular docking and Site Finder module defined the thieno[2,3-d]pyrimidines interactions with the most important catalytic residues of DNase I, including Glu 39, His 134, Asp 168 and His 252. We also found that steric effects and increase of molecular volume play a vital role in DNase I inhibition.

Synthesis of novel 5-aryl/hetarylidenyl 3-(2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-thioxothiazolidin-4-ones

The synthesis of a variety of novel 5-substituted titled compounds containing a priviledged rhodanine scaffold is described. The synthesis involves a microwave (MW) assisted Knoevenagel condensation of 3-(2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-thioxothiazolidin-4-one with suitably substituted aromatic aldehydes. However, these condensations fail with aliphatic aldehydes. The 2-thioxothiazolidin-4-one (rhodanine) precursor was prepared by the condensation of 2-thioxothiazolidin-4-one-di-(carboxymethyl)trithiocarbonyl and 4,5,6,7-tetrahydrobenzo[4,5]thienyl[2,3-d]-2-methylpyrimidin-4-amine in the presence of K2CO3.

Reaction of Nitriles under Acidic Conditions. Part VI. Synthesis of Condensed 4-Chloro- and 4-Aminopyrimidines from ortho-Aminonitriles

Condensation of a nitrile with benzene, furan and thiophene ortho-aminonitriles in the presence of dry hydrogen chloride yields condensed 4-chloropyrimidines, condensed 4-aminopyrimidines or a mixture of the two condensed pyrimidines in varying proportions depending upon the nature of the nitrile and the substrate, ortho-aminonitrile.