1422427-71-1

Basic information

• Product Name: 8-(3-chlorophenyl)pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-amine
• Synonyms: 8-(3-chlorophenyl)pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-amine
• CAS NO: 1422427-71-1
• Molecular Weight: 312.782
• Mol File: 1422427-71-1.mol

Chemical Properties

• CAS DataBase Reference: 8-(3-chlorophenyl)pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(3-chlorophenyl)pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-amine(1422427-71-1)
• EPA Substance Registry System: 8-(3-chlorophenyl)pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-amine(1422427-71-1)

Safety Data

• Hazardous Substances Data: 1422427-71-1(Hazardous Substances Data)

Upstream product

• 1422427-65-3 (E)-N'-(5-(3-chlorophenyl)-2-cyanothieno[2,3-b]pyridin-3-yl)-N,N-dimethylformimidamide 
• 77287-34-4 formamide 
• 1422427-60-8 (E)-N′-(5-bromo-2-cyanothieno[2,3-b]pyridin-3-yl)-N,N-dimethylformimidamide 
• 405224-23-9 5-bromo-2-chloropyridine-3-carbonitrile 
• 1422427-59-5 3-amino-5-bromothieno[2,3-b]pyridine-2-carbonitrile 

Relevant articles and documents

Synthesis and molecular modelling studies of 8-arylpyrido[30,20:4,5] thieno[3,2-d]pyrimidin-4-amines as multitarget Ser/Thr kinases inhibitors

This paper reports the design and synthesis of a novel series of 8-arylpyrido[3g2,2g2:4,5]thieno[3,2-d]pyrimidin-4-amines via microwave-assisted multi-step synthesis. A common precursor of the whole series, 3-amino-5-bromothieno[2,3-b]pyridine-2-carbonitrile, was rapidly synthesized in one step from commercially-available 5-bromo-2-chloronicotinonitrile. Formylation with DMF-DMA led to (E)-Ng2-(5-bromo-2-cyanothieno[2,3-b]pyridin-3-yl)-N,N-dimethylformimidamide (4) which was conveniently functionalized at position 8 by palladium-catalyzed Suzuki-Miyaura cross-coupling to introduce a heteroaromatic ring. High-temperature formamide-mediated cyclization of the cyanoamidine intermediate gave seventeen 8-arylpyrido[3g2,2g2:4,5]thieno[3,2-d]pyrimidin-4-amines. The inhibitory potency of the final products was evaluated against five protein kinases (CDK5/p25, CK1δ/, GSK3α/β, DYRK1A and CLK1) and revealed that 8-(2,4-dichlorophenyl)pyrido[3g2,2g2:4,5]thieno[3,2-d]pyrimidin-4-amine 1g specifically inhibits CK1 δ and CLK1 (220 and 88 nM, respectively) while its 7-(2,4-dichlorophenyl)pyrido[3g2,2g2:4,5]thieno[3,2-d]pyrimidin-4-amine isomer 10 showed no activity on the panel of tested kinases. Molecular modelling of 10 and 1g in the ATP binding sites of CK1 δ/and CLK1 showed that functionalization at position 7 of pyrido[3g2,2g2:4,5]thieno[3,2-d]pyrimidin-4-amines is likely to induce a steric clash on the CK1 δ/epies; P-loop and thus a complete loss of inhibitory activity.

Suzuki cross-coupling of 5-bromothieno[2,3-b]pyridines for the convenient synthesis of 8-arylpyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4-amines

For the first time, Suzuki cross-coupling reactions were used for introducing an aromatic group in position 8 of the pyridine ring of novel pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4-amines. This reliable and simple method may be extended to various boronic acids for allowing preparation of a larger library of these compounds in the hope of further structure-activity relationship investigations.