Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate

Name: Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate
Brand: ChemScene
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CAS No. 583878-42-6
Cat. No. CS-W022690
Molecule weightNone
Purity≥97%
MDL No.MFCD08063161

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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+
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Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate|CS-W022690

Structure of 583878-42-6

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General Information

CAS No. 583878-42-6
Cat. No. CS-W022690
Purity ≥97%
MDL No. MFCD08063161
Storage -20°C, stored under nitrogen, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₁ClN₂O₂S
Molecular Weight None
Synonym(s) Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate
SMILES CCOC(=O)C1=C(Cl)N=C(SC)N=C1C

Description

Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate features a sterically hindered pyrimidine core with orthogonal functional handles: a chloro group at C4, a methylthio substituent at C2, and a methylated ester at C5. This configuration enables direct coupling in cross-coupling protocols and facilitates downstream derivatization under mild conditions. The compound exhibits high bench stability and solubility in common organic solvents.

Application

Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyrimidines via nucleophilic displacement and cross-coupling reactions. The chloro group at C4 facilitates regioselective functionalization, while the methylthio and ester functionalities offer orthogonal reactivity for downstream transformations. Its bench-stable nature and compatibility with standard synthetic protocols make it well-suited for medicinal chemistry campaigns and process development.

Synthesis

Route1
- In-stock
  
  344361-90-6
- ~98%
- In-stock
  
  583878-42-6
References
- GENOSCO; OSCOTEC INC.; KIM, Hong, Woo; KOH, Jong, Sung; LEE, Jaekyoo; SONG, Ho-Juhn; KIM, Youngsam; LEE, Hee, Kyu; CHOI, Jang-Sik; LIM, Sun-Hee; CHANG, Sunhwa Patent: WO2011/53861 A1, 2011 ; Location in patent: Page/Page column 46 ; WO 2011/053861 A1
Route2
- In-stock
  
  1462-12-0
- ~%
- In-stock
  
  583878-42-6
References
- Tetrahedron Letters, , vol. 46, # 50 p. 8749 - 8752

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 52.08
LogP 2.33702
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate

CAS No. 583878-42-6

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