5-Bromo-4-methoxypyrimidine

Name: 5-Bromo-4-methoxypyrimidine
Brand: ChemScene
Availability: InStock
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CAS No. 4319-85-1
Cat. No. CS-W005510
Purity≥98%
MDL No.MFCD00234066

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Structure of 4319-85-1

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General Information

CAS No. 4319-85-1
Cat. No. CS-W005510
Purity ≥98%
MDL No. MFCD00234066
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₅BrN₂O
Molecular Weight 189.01
Synonym(s) None
SMILES COC1=NC=NC=C1Br

Description

5-Bromo-4-methoxypyrimidine is a bench-stable pyrimidine derivative featuring a bromine atom at the 5-position and a methoxy group at the 4-position. This electron-deficient heterocycle facilitates direct functionalization in cross-coupling reactions, enabling efficient access to substituted pyrimidines. The para-methoxy substituent enhances solubility and modulates reactivity.

Application

5-Bromo-4-methoxypyrimidine serves as a versatile building block in medicinal chemistry, enabling efficient access to pyrimidine-based scaffolds through palladium-catalyzed cross-coupling reactions. Its bromine substituent facilitates reliable C–C and C–N bond formation under standard conditions, while the methoxy group enhances solubility and provides orthogonal reactivity. The compound exhibits excellent bench stability and is readily purified by recrystallization or flash chromatography, making it ideal for high-throughput synthesis of kinase inhibitors and other bioactive heterocycles.

Synthesis

Route1
- 67-56-1
- ~%
- In-stock
  
  4319-85-1
References
- Amgen Inc. Patent: US2006/199817 A1, 2006 ; Location in patent: Page/Page column 49 ; US 20060199817 A1
Route2
- In-stock
  
  19808-30-1
- 67-56-1
- ~%
- In-stock
  
  4319-85-1
References
- NOVARTIS AG; Cotesta, Simona; Furet, Pascal; Guagnano, Vito; Holzer, Philipp; Kallen, Joerg; Mah, Robert; Masuya, Keiichi; Schlapbach, Achim; Stutz, Stefan; Vaupel, Andrea Patent: US2013/317024 A1, 2013 ; Location in patent: Paragraph 0753; 0754 ;

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 35.01
LogP 1.2477
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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5-Bromo-4-methoxypyrimidine

CAS No. 4319-85-1

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