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

General Description

6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one is a chemical compound that belongs to the pyrazole class of molecules. It has the molecular formula C6H6N4O and a molecular weight of 150.14 g/mol. 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one is a heterocyclic organic molecule that contains both nitrogen and oxygen atoms within its structure. It is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals due to its versatile reactivity and ability to participate in various chemical reactions. It has potential applications in the field of medicinal chemistry and drug discovery as a starting material for the development of novel therapeutic agents. Additionally, it may also have uses in other industrial processes and research applications due to its unique chemical properties.

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

• 100644-65-3 4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine 
• 42754-96-1 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine 
• 2465-59-0 oxypurinol 
• 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 
• 42754-97-2 6-chloro-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 

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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