2537-04-4

Basic information

• Product Name: 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one
• Synonyms: 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one;6-amino-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one;6-Amino-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one;4-Hydroxy-6-aminopyrazolo[3,4-d]pyrimidine;4-Oxo-6-aminopyrazolo[3,4-d]pyrimidine;8-Aza-7-deazaguanine;HAPP;NSC 760
• CAS NO: 2537-04-4
• Molecular Formula: C5H5N5O
• Molecular Weight: 151
• Mol File: 2537-04-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 351.9°C at 760 mmHg
• Flash Point: 166.6°C
• Appearance: /
• Density: 2.19g/cm³
• Vapor Pressure: 3.98E-05mmHg at 25°C
• Refractive Index: 2.047
• CAS DataBase Reference: 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one(2537-04-4)
• EPA Substance Registry System: 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one(2537-04-4)

Safety Data

• Hazardous Substances Data: 2537-04-4(Hazardous Substances Data)

Usage

Description

6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one is a heterocyclic organic molecule belonging to the pyrazole class of compounds. It features a molecular formula of C6H6N4O and a molecular weight of 150.14 g/mol. This versatile molecule contains both nitrogen and oxygen atoms within its structure, making it a valuable building block in the synthesis of pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity allow it to participate in a wide range of chemical reactions, making it a promising candidate for the development of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one serves as a crucial component in the creation of new agrochemicals. Its ability to engage in diverse chemical reactions contributes to the development of innovative products for agricultural applications.
Used in Medicinal Chemistry and Drug Discovery:
6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one is employed as a starting material in medicinal chemistry and drug discovery. Its potential applications in this field stem from its unique chemical properties, which facilitate the design and synthesis of new compounds with therapeutic potential.
Used in Industrial Processes and Research Applications:
Due to its distinctive chemical characteristics, 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one may also find uses in other industrial processes and research applications. Its versatility and reactivity make it a valuable asset in the development of new technologies and scientific advancements.

InChI:InChI=1/C5H5N5O/c6-5-8-3-2(1-7-10-3)4(11)9-5/h1H,(H4,6,7,8,9,10,11)

Upstream product

• 42754-97-2 6-chloro-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 100644-65-3 4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine 
• 100644-70-0 8-aza-7-deaza-2'-deoxyguanosine 
• 109737-94-2 6-Amino-2-(2'-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo<3,4-d>pyrimidin-4(5H)-one 
• 2465-59-0 oxypurinol 
• 42754-96-1 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine 

Downstream Products

• 144772-49-6 N-<4-<2-(2-Amino-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamic acid 
• 144772-48-5 Dimethyl N-<4-<2-(2-amino-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate 
• 144750-85-6 Dimethyl N-<4-<2-(2-amino-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate 

Relevant articles and documents

HETEROCYCLIC GTP CYCLOHYDROLASE 1 INHIBITORS FOR THE TREATMENT OF PAIN

The present invention relates to the field of small molecule heterocyclic inhibitors of GTP cyclohydrolase (GCH-I), or a tautomer, prodrug, or pharmaceutically acceptable salt thereof. The invention also features pharmaceutical compositions of the compounds and the medical use of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, or neuropathic pain).

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.

Synthesis of 2'-deoxyribofuranosides of 8-aza-7-deazaguanine and related pyrazolo[3,4-d]pyrimidines

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