203180-01-2

Basic information

• Product Name: 3-iodo-4-methoxy-1H-Pyrazolo[3,4-d]pyrimidin-6-amine
• Synonyms: 3-iodo-4-methoxy-1H-Pyrazolo[3,4-d]pyrimidin-6-amine;6-Amino-3-iodo-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine
• CAS NO: 203180-01-2
• Molecular Formula: C₆H₆IN₅O
• Molecular Weight: 291.04921
• Mol File: 203180-01-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-iodo-4-methoxy-1H-Pyrazolo[3,4-d]pyrimidin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-iodo-4-methoxy-1H-Pyrazolo[3,4-d]pyrimidin-6-amine(203180-01-2)
• EPA Substance Registry System: 3-iodo-4-methoxy-1H-Pyrazolo[3,4-d]pyrimidin-6-amine(203180-01-2)

Safety Data

• Hazardous Substances Data: 203180-01-2(Hazardous Substances Data)

Upstream product

• 100644-67-5 6-amino-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine 
• 100644-67-5 4-Methoxy-pyrazolo[3,4-d]pyrimidin-6-ylamine 
• 5604-46-6 2-amino-4,6-dichloropyrimidine-5-carboxaldehyde 
• 100644-65-3 4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine 

Downstream Products

• 109737-90-8 6-amino-1-[2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine 
• 203180-05-6 6-Amino-1-[2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-3-iodo-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine 

Relevant articles and documents

nitrogen hybridization guanine nucleoside and its synthetic method and the use of DNA sequencing

The invention discloses hybrid azaguanosine as well as a synthesis method and an application thereof in DNA sequencing. The synthesis method comprises the steps: removing a protecting group of a compound as shown in formula (III) in the specification under an alkaline condition to obtain a compound as shown in formula (II) in the specification; further demethylating to obtain a compound as shown in formula (I) in the specification, i.e. 7-deaza-7-halogen-8-aza-guanosine, wherein R1 is H or OH, R2 is I, Br or Cl, and R3 is H or a compound shown in the specification. The hybrid azaguanosine disclosed by the invention is a novel reagent for DNA sequencing, which, compared to guanosine failing to substitute nitrogen on 8 sites, is more excellent in base identifying effect and more stable in DNA chain structure. Meanwhile, different from the prior art that 8-site nitrogen-substituted guanosine is complex in synthesis method, low in yield and unsuitable for commercial production, the synthesis method disclosed by the invention is easily available in raw material required, and adopts conventional chemical synthesis reaction; and the method is relatively high in yield, and suitable for wide popularization and application.

Modified oligonucleotides for mismatch discrimination

Modified oligonucleotides are provided containing bases selected from unsubstituted and 3-substituted pyrazolo[3,4-d]pyrimidines and 5-substituted pyrimidines, and optionally have attached minor groove binders and reporter groups.

Process for the synthesis of pyrazolopyrimidines

The present invention provides a nucleoside comprising a pyrazolopyrimidine base and a process for producing the same. In particular, the processes of the present invention comprises using a halogenated pyrazolopyrimidine base and removing the halogen after the base is coupled to a sugar moiety. The presence of the halogen on the nucleoside base allows facile and economical production of a large quantity of nucleosides.

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.