4-Chloro-5H-pyrrolo[3,2-d]pyrimidine

Name: 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 84905-80-6
Cat. No. CS-M3333
Purity≥95%
MDL No.MFCD06658411

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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4-Chloro-5H-pyrrolo[3,2-d]pyrimidine|CS-M3333

Structure of 84905-80-6

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General Information

CAS No. 84905-80-6
Cat. No. CS-M3333
Purity ≥95%
MDL No. MFCD06658411
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄ClN₃
Molecular Weight 153.57
Synonym(s) 6-chloro-9-deaza-7H-purine, 4-chloro-3H,5H-pyrrolo[3,2-d]pyriMidine, 4-ChloropyrrolopyriMidine; 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine
SMILES ClC1=NC=NC2=C1NC=C2

Description

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine is a heterocyclic building block featuring a chlorinated pyrrolopyrimidine core. This electron-deficient scaffold integrates readily into medicinal chemistry campaigns, enabling direct functionalization at the 5-position. The molecule exhibits robust stability under standard bench conditions and serves as a key intermediate in the synthesis of kinase inhibitors and nucleoside analogs.

Application

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient access to purine analogs through nucleophilic substitution. Its chlorine atom at the 4-position facilitates regioselective coupling with diverse amines and thiols, offering reliable functionalization under mild conditions. The scaffold exhibits good bench stability and compatibility with common protecting groups, making it well-suited for iterative synthesis of kinase inhibitors and antiviral agents.

Synthesis

Route1
- In-stock
  
  5655-01-6
- ~97%
- In-stock
  
  84905-80-6
References
- Organic Process Research and Development, , vol. 13, # 5 p. 928 - 932
Route2
- In-stock
  
  252932-48-2
- ~%
- In-stock
  
  84905-80-6
References
- US2012/202785 A1, ;
Route3
- 1021175-71-2
- ~%
- In-stock
  
  84905-80-6
References
- US2012/202785 A1, ;

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

Quality Control

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Computational Chemistry Data

TPSA 41.57
LogP 1.6113
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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4-Chloro-5H-pyrrolo[3,2-d]pyrimidine

CAS No. 84905-80-6

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