5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

Name: 5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine
Brand: ChemScene
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CAS No. 900789-14-2
Cat. No. CS-0045864
Purity≥95%
MDL No.MFCD13193619

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5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine|CS-0045864

Structure of 900789-14-2

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General Information

CAS No. 900789-14-2
Cat. No. CS-0045864
Purity ≥95%
MDL No. MFCD13193619
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₂BrCl₂N₃
Molecular Weight None
Synonym(s) None
SMILES ClC1=C2C(NC=C2Br)=NC(Cl)=N1

Description

5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine features a highly reactive pyrrolopyrimidine core with complementary halogen sites for selective cross-coupling. This electron-deficient scaffold enables efficient functionalization in late-stage diversification, particularly in kinase inhibitor and nucleoside analog synthesis.

Application

5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine serves as a versatile building block in medicinal chemistry, enabling efficient construction of purine-like scaffolds. The bromo and dichloro substituents provide orthogonal functional handles for palladium-catalyzed cross-coupling and nucleophilic substitution reactions. Its bench-stable crystalline form facilitates handling and purification, while the electron-deficient heterocyclic core supports diverse derivatization pathways relevant to kinase inhibitor and antiviral agent development.

Synthesis

Route1
- 90213-66-4
- ~69%
- In-stock
  
  900789-14-2
References
- Seela, Frank; Xu, Kuiying Helvetica Chimica Acta, 2008 , vol. 91, # 6 p. 1083 - 1105

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 41.57
LogP 3.0272
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

CAS No. 900789-14-2

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