183274-50-2

Basic information

• Product Name: 1H-Pyrazolo[3,4-d]pyriMidin-6-aMine, 3-broMo-4-(1-Methylethoxy)-
• Synonyms: 1H-Pyrazolo[3,4-d]pyriMidin-6-aMine, 3-broMo-4-(1-Methylethoxy)-;3-Bromo-4-(propan-2-yloxy)-1H-pyrazolo[3,4-d]pyrimidin-6-amine;3-BroMo-4-isopropoxy-1H-pyrazolo[3,4-d]pyriMidin-6-aMine
• CAS NO: 183274-50-2
• Molecular Formula: C₈H₁₀BrN₅O
• Molecular Weight: 272.1019
• Mol File: 183274-50-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrazolo[3,4-d]pyriMidin-6-aMine, 3-broMo-4-(1-Methylethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazolo[3,4-d]pyriMidin-6-aMine, 3-broMo-4-(1-Methylethoxy)-(183274-50-2)
• EPA Substance Registry System: 1H-Pyrazolo[3,4-d]pyriMidin-6-aMine, 3-broMo-4-(1-Methylethoxy)-(183274-50-2)

Safety Data

• Hazardous Substances Data: 183274-50-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
1H-Pyrazolo[3,4-d]pyrimidin-6-amine, 3-bromo-4-(1-methylethoxy)is utilized as a chemical intermediate for the synthesis of novel pharmaceutical compounds. Its unique structure, including the brominated pyrazolopyrimidine core and the amine and methylethoxy substituents, may contribute to the development of new drugs with distinct biological activities and therapeutic benefits.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1H-Pyrazolo[3,4-d]pyrimidin-6-amine, 3-bromo-4-(1-methylethoxy)serves as a key building block for the design and synthesis of new bioactive molecules. Its structural features can be exploited to create compounds with improved pharmacokinetic and pharmacodynamic profiles, enhancing their efficacy and safety in treating various diseases.
Used in Drug Discovery:
1H-Pyrazolo[3,4-d]pyrimidin-6-amine, 3-bromo-4-(1-methylethoxy)is employed as a starting material in drug discovery programs, where it can be further modified and optimized to generate lead compounds with potential therapeutic applications. Its unique structural elements can be leveraged to discover new chemical entities with novel mechanisms of action and improved drug-like properties.
Used in Biochemical Studies:
1H-Pyrazolo[3,4-d]pyrimidin-6-amine, 3-bromo-4-(1-methylethoxy)can also be used in biochemical studies to investigate its interactions with various biological targets, such as enzymes, receptors, or other proteins. Understanding these interactions can provide valuable insights into the molecular mechanisms underlying its potential biological activities and guide the development of more effective and selective therapeutic agents.

InChI:InChI=1S/C8H10BrN5O/c1-3(2)15-7-4-5(9)13-14-6(4)11-8(10)12-7/h3H,1-2H3,(H3,10,11,12,13,14)

Upstream product

• 100644-65-3 4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine 
• 183274-49-9 4-Isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine 

Downstream Products

• 190430-38-7 6-amino-3-bromo-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine 
• 190430-41-2 2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-2H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 577992-09-7 3-bromo-2-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 577990-95-5 3-bromo-1-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 190430-40-1 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine 

Relevant articles and documents

Synthesis of 7-halogenated 8-aza-7-deaza-2'-deoxyguanosines and related pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides

The synthesis of 7-bromo and 7-iodo derivatives of 8-aza-7-deaza-2'- deoxyguanosine (2, 3) as well as the halogenated 4-alkoxy derivatives 4a-c and 5a-c is described. Glycosylation of the halogenated pyrazolo[3,4- d]pyrimidine anions of 7a-c or 8a-c with 2-deoxy-3,5-di-O-(p-toluoy)-α-D- erythro-pentofuranosyl chloride (9) yields regioisomeric glycosylation products, the N(1)-isomers 10a-c and 11a-c as well sa the N(2)-compounds 12a- c. The latter isomers lose their halogen during the glycosylation in the presence of non-anhydrous KOH. Anhydrous conditions (NaH) furnished 10c, 11c together with the halogenated N(2)-isomers 13a,b. Compounds 10a-c, and 11a-c were deprotected and converted to the 4-alkoxy nucleosides 4a-c and 5a-c. The N(1)-nucleosides 4c and 5c were hydrolyzed to give the 7-bromo or 7-iodo derivatives of 8-aza-7-deaza-2'-deoxyguanosines 2 and 3. Different from regular 2'-deoxyribonucleosides the sugar moiety of pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides shows a preferred N-type pucker (3T2) in solution, a conformation which is also detected in the solid state.

Unexpected dehalogenation of 3-bromopyrazolo[3,4-d]pyrimidine nucleosides during nucleobase-anion glycosylation

The anion-glycosylation (KOH, MeCN, TDA-1) of 3-bromopyrazolo[3,4-d]- pyrimidines 4a and 4b with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro- pentofuranosyl chloride (5) furnishes the regioisomeric N1-β-D-2'- deoxyribonucleosides 6a and 6b together with the dehalogenated N2- regioisomers 8a and 8b, stereoselectively. The dehalogenation takes place after the glycosylation and results from the sensitivity of the N-2 nucleosides toward aqueous base. An addition/elimination mechanism is suggested for the dehalogenation reaction.

7-Deazapurine DNA: Oligonuvleotides Containing 7-Substituted 7-Deaza-2'-deoxyguanosine and 8-Aza-7-deaza-2'-deoxyguanosine

The synthesis of 7-halogeno substituted 7-deaza- and 8-aza-7-deaza-2'-deoxyguanosines, their incorporation into oligonucleotides, and the stability of corresponding duplexes are described.