Tert-butyl 6-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Name: Tert-butyl 6-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
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CAS No. 2250061-21-1
Cat. No. CS-0179667
Purity≥95%
MDL No.None

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Tert-butyl 6-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate|CS-0179667

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General Information

CAS No. 2250061-21-1
Cat. No. CS-0179667
Purity ≥95%
MDL No. None
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₃IN₆O₂
Molecular Weight 506.34
Synonym(s) None
SMILES O=C(N1CC2=C(C=C(CN3N=C(I)C4=C(N)N=CN=C43)C=C2)CC1)OC(C)(C)C

Description

Tert-butyl 6-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate features a pyrazolopyrimidine core paired with a dihydroisoquinoline scaffold, enabling direct integration into kinase inhibitor scaffolds. The pendant tert-butyl ester supports facile deprotection under mild acidic conditions, while the iodo and amino groups provide orthogonal handles for downstream functionalization via cross-coupling or nucleophilic substitution. This compound serves as a key intermediate in the synthesis of bioactive heterocycles.

Application

Tert-butyl 6-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate serves as a versatile building block for the synthesis of biologically active heterocycles. The pyrazolopyrimidine core enables efficient metal-catalyzed cross-coupling reactions, while the dihydroisoquinoline scaffold provides structural rigidity and enhanced solubility. The tert-butyl ester group offers bench stability and facile deprotection under mild acidic conditions, facilitating downstream functionalization. This compound functions effectively in standard coupling protocols and supports the construction of complex scaffolds relevant to medicinal chemistry campaigns.

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 99.16
LogP 3.3546
H_Acceptors 7
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Iodide

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Tetrahydroisoquinoline compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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Tert-butyl 6-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

CAS No. 2250061-21-1

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