3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Name: 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Brand: ChemScene
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CAS No. 83255-86-1
Cat. No. CS-W008671
Molecule weight214.02
Purity≥97%
MDL No.MFCD12196922

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3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine|CS-W008671

Structure of 83255-86-1

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General Information

CAS No. 83255-86-1
Cat. No. CS-W008671
Purity ≥97%
MDL No. MFCD12196922
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₄BrN₅
Molecular Weight 214.02
Synonym(s) NSC 370384; 7-Bromo-2,4,8,9-Tetrazabicyclo[4.3.0]Nona-2,4,6,9-Tetraen-5-Amine
SMILES NC1=C2C(NN=C2Br)=NC=N1

Description

3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine features a brominated pyrazolopyrimidine core with a primary amine at the 4-position, enabling direct coupling in cross-coupling reactions. The electron-deficient heterocycle facilitates efficient functionalization, while the bromide serves as a reactive handle for palladium-catalyzed transformations. This scaffold exhibits excellent stability under standard conditions and integrates readily into medicinal chemistry campaigns targeting kinase inhibitors and nucleoside analogs.

Application

3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine serves as a versatile building block for purine-derived heterocycles, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling. The bromo group facilitates Suzuki, Stille, and Buchwald-Hartwig reactions, while the pyrazolo[3,4-d]pyrimidine core provides a stable scaffold with enhanced solubility and metabolic resistance. Bench-stable and readily purified by flash chromatography, it functions as a key intermediate in the synthesis of kinase inhibitors and nucleoside analogs.

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 80.48
LogP 0.6976
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

CAS No. 83255-86-1

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