4-Chloro-6-methoxypyrimidine

Name: 4-Chloro-6-methoxypyrimidine
Brand: ChemScene
Availability: InStock
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CAS No. 26452-81-3
Cat. No. CS-D1580
Purity≥98%
MDL No.MFCD06200211

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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+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 26452-81-3

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General Information

CAS No. 26452-81-3
Cat. No. CS-D1580
Purity ≥98%
MDL No. MFCD06200211
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₅ClN₂O
Molecular Weight 144.56
Synonym(s) Pyrimidine, 4-chloro-6-methoxy-
SMILES COC1=CC(Cl)=NC=N1

Description

4-Chloro-6-methoxypyrimidine features a pyrimidine core with complementary electron-withdrawing and donating substituents, enabling selective functionalization at C5. This bench-stable heterocycle integrates efficiently into pharmaceutical intermediates, where the chlorine facilitates nucleophilic substitution and the methoxy group enhances solubility and regiocontrol during synthesis.

Application

4-Chloro-6-methoxypyrimidine serves as a versatile building block in medicinal chemistry, enabling efficient construction of pyrimidine-based scaffolds. The chloro group at C4 facilitates nucleophilic substitution reactions with amines, thiols, and other heteroatom nucleophiles, while the methoxy substituent at C6 enhances solubility and modulates electronic properties. This compound exhibits excellent bench stability and compatibility with standard coupling protocols, making it well-suited for modular synthesis of bioactive molecules and API intermediates.

Synthesis

Route1
- 67-56-1
- In-stock
  
  1193-21-1
- ~93%
- In-stock
  
  26452-81-3
References
- Zhou, Bishan; Taylor, Brett; Kornau, Kathryn Tetrahedron Letters, 2005 , vol. 46, # 23 p. 3977 - 3979
Route2
- In-stock
  
  1193-21-1
- 124-41-4
- ~%
- In-stock
  
  26452-81-3
References
- BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus Patent: WO2013/79460 A1, 2013 ; Location in patent: Page/Page column 44 ;
Route3
- In-stock
  
  1193-21-1
- ~%
- In-stock
  
  26452-81-3
References
- Hoechst Aktiengesellschaft Patent: US5668140 A1, 1997 ;

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 35.01
LogP 1.1386
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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4-Chloro-6-methoxypyrimidine

CAS No. 26452-81-3

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