852313-98-5

Upstream product

• 1006597-09-6 C₁₁H₇ClN₄O 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 41052-75-9 o-chlorophenylhydrazine hydrochloride 
• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 1429924-47-9 4,6-dichloro-5-{(E)-[(2-chlorophenyl)hydrazono]methyl}pyrimidine 
• 792953-14-1 5-amino-1-(2-chloro-phenyl)-1H-pyrazole-4-carboxylic acid amide 
• 64096-89-5 5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile 
• 1006597-09-6 1-(2-chloro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 

Downstream Products

• 955305-69-8 C₁₇H₁₈ClN₅ 
• 1207831-40-0 N-[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]glycine 
• 1207760-38-0 2-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-3-methoxy-N-(5-methylpyridin-2-yl)propanamide 
• 1207826-70-7 (2S)-2-[1-(2-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxy-N-(3-methyl-1,2,4-thiadiazol-5-yl)-3-propan-2-yloxypropanamide 
• 1207826-72-9 (2S)-2-(1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-methoxy-N-(3-methyl-1,2,4-thiadiazol-5-yl)propanamide 
• 1207826-81-0 (2S)-2-[1-(2-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxy-3-ethoxy-N-(5-methylpyrazin-2-yl)propanamide 
• 1207827-47-1 (2S)-2-[1-(2-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxy-3-(cyclobutoxy)-N-(5-methylpyrazin-2-yl)propanamide 
• 1207828-47-4 (2S)-2-[1-(2-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxy-3-[(1S)-2-methoxy-1-methyl-ethoxy]-N-(5-methylpyrazin-2-yl)propanamide 
• 1207828-49-6 (2S)-2-[1-(2-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxy-3-[(1S)-2-methoxy-1-methyl-ethoxy]-N-(5-methyl-2-pyridyl)propanamide 
• 1207830-71-4 (2S)-3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-2-(1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-methylpyrazin-2-yl)propanamide 
• 1207761-11-2 2-(1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-methyl-N-(5-methylpyridin-2-yl)butanamide 
• 1207760-42-6 (S)-2-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-3-methoxy-N-(5-methylpyridin-2-yl)propanamide 
• 1207760-41-5 (R)-2-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-3-methoxy-N-(5-methylpyridin-2-yl)propanamide 
• 1207760-58-4 2-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-4-methoxy-N-(5-methylpyridin-2-yl)butanamide 

Relevant academic research and scientific papers

Synthesis of 1,4-disubstituted pyrazolo[3,4-d]pyrimidines from 4,6-dichloropyrimidine-5-carboxaldehyde: Insights into selectivity and reactivity

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5- carboxaldehyde with both aromatic and aliphatic hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective, high-yielding, and operationally simple manner are presented. For aromatic hydrazines, the reaction is performed at a high temperature in the absence of an external base. For aliphatic hydrazines, the reaction proceeds at room temperature in the presence of an external base. The observed selectivity and reactivity trends are rationalized through consideration of the proposed reaction mechanism. The 1-substituted 4-chloropyrazolo[3,4-d]pyrimidine products serve as versatile synthetic intermediates, through further functionalization of the 4-chloride moiety, enabling the rapid generation of a structurally diverse array of 1,4-disubstituted pyrazolo[3,4-d]pyrimidines. Georg Thieme Verlag Stuttgart. New York.

Selective synthesis of 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5- carboxaldehyde with various hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective and high-yielding manner are presented. For aromatic hydrazines, the reaction is performed in the absence of an external base, which promotes exclusive hydrazone formation. The hydrazones subsequently cyclize at an elevated temperature to form the desired pyrazolo[3,4-d]pyrimidine products. For aliphatic hydrazines, the reaction sequence proceeds as a single step in the presence of an external base.

The discovery of a novel series of glucokinase activators based on a pyrazolopyrimidine scaffold

Glucokinase is a key enzyme in glucose homeostasis since it phosphorylates glucose to give glucose-6-phosphate, which is the first step in glycolysis. GK activators have been proven to lower blood-glucose, and therefore have potential as treatments for type 2 diabetes. Here the discovery of pyrazolopyrimidine GKAs is reported. An original singleton hit from a high-throughput screen with micromolar levels of potency was optimised to give compounds with nanomolar activities. Key steps in this success were the introduction of an extra side-chain, which increased potency, and changing the linking functionality from a thioether to an ether, which led to improved potency and lipophilic ligand efficiency. This also led to more stable compounds with improved profiles in biological assays.

Microwave-assisted protocols for the expedited synthesis of pyrazolo[1,5-a] and [3,4-d]pyrimidines

General, high-yielding MAOS protocols for the expedited synthesis of functionalized pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-b]pyrimidines, as well as their pyrazole precursors, are described amenable to an iterative analogue library synthesis strategy for lead optimization.

Positive allosteric modulators of the metabotropic glutamate receptor subtype 4 (mGluR4): Part I. Discovery of pyrazolo[3,4-d]pyrimidines as novel mGluR4 positive allosteric modulators

This letter describes the synthesis and SAR, developed through an iterative analogue library approach, of an mGluR4 positive allosteric modulator lead based on a pyrazolo[3,4-d]pyrimidine scaffold. Despite tremendous therapeutic potential, Compound 7, VU0080421, and related congeners represent only a handful of mGluR4 positive allosteric modulators ever described.

Aryl substituted purine analogues

Aryl-substituted purine analogues are provided, of the formula: (I) wherein variables are as described herein. Such compounds are ligands that may be used to modulate specific receptor activity in vivo or in vitro, and are particularly useful in the treat

PYRAZOLOPYRIMIDINES AS ANTI - HEPATITS C AGENTS

Pyrazolopyrimidine derivatives of formula (I), or a pharmaceutically acceptable salt thereof, are found to be active against hepatitis C infection, wherein: R1 is C6-C10 aryl, 5- to 10- membered heteroary1, -(C1-C4 alkyl)-(C6-C10 aryl) or -(C1-C4 alkyl)-(5- to 10- membered heteroaryl); R2 is a C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heteroaryl or 5- to 10- membered heterocyclyl moiety, said moiety being optionally fused to a C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heteroaryl or 5- to 10-membered heterocyclic ring; and X is -NR'-, -NR'-CO-NR''-, -NR'-L, or -NR'-CO-L-, wherein R' and R'' are the same or different and each represent hydrogen or a C1-C6 alkyl group and L represents a C1-C6 alkylene group, the aryl, heteroaryl, heterocyclyl. and carbocyclyl moieties in the R1 and R2 substituents being unsubstituted or substituted by 1, 2 or 3 substituents selected from halogen, C1-C4 alkyl C1-C4alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano, nitro, C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heterocyclyl, 5- to 10- membered heteroaryl, -NR'-CO2-R'', -CO2R'', -COR'''-NR'-CO-R''',-CONR'R'',SO2NR'R'',SO2R'''and -O-(CH2)n-R''' substituents, wherein n is from 0 to 4, each R’is the same or different and is hydrogen or C1-C6 alkyl, each R'' is the same or different and is hydrogen, C1-C6 alkyl, C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heteroaryl, each R''' is the same or different and is C1-C6 alkyl, C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heteroaryl, and each R'''' is the same or different and is C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heterocryl, the aryl, heteroaryl, heterocyclyl and carbocyclyl moieties in said substituents being unsubstituted or substituted by a further substituent selected from C1-C4 alkyl, C1-C4 hydroxyalkyl and C1-C4 haloalkyl groups.