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2-CHLOROPYRIMIDINE-4-CARBOXAMIDE

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2-CHLOROPYRIMIDINE-4-CARBOXAMIDE Basic information

Product Name:
2-CHLOROPYRIMIDINE-4-CARBOXAMIDE
Synonyms:
  • 4-(Aminocarbonyl)-2-chloropyrimidine, 4-Carbamoyl-2-chloropyrimidine
  • 2-Chloro-pyrimidine-4-carboxylic acid amide
  • 2-CHLOROPYRIMIDINE-4-CARBOXAMIDE
  • NSC 60802
  • 2-chloro-4-Pyrimidinecarboxamide
  • 4-Pyrimidinecarboxamide, 2-chloro-
CAS:
22536-66-9
MF:
C5H4ClN3O
MW:
157.56
Product Categories:
  • Building Blocks
  • Pyrimidine
Mol File:
22536-66-9.mol
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2-CHLOROPYRIMIDINE-4-CARBOXAMIDE Chemical Properties

storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
form 
solid
Appearance
White to off-white Solid
InChI
InChI=1S/C5H4ClN3O/c6-5-8-2-1-3(9-5)4(7)10/h1-2H,(H2,7,10)
InChIKey
UXXQEVFRPLIOHJ-UHFFFAOYSA-N
SMILES
C1(Cl)=NC=CC(C(N)=O)=N1
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
26-36
HS Code 
29242990
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2-CHLOROPYRIMIDINE-4-CARBOXAMIDE Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

2-Chloropyrimidine-4-carboxamide is used as an organic synthesis and pharmaceutical intermediate.

Synthesis

149849-92-3

22536-66-9

General procedure for the synthesis of 2-chloropyrimidine-4-carboxamide from 2-chloropyrimidine-4-carboxylic acid: 2-chloropyrimidine-4-carboxylic acid (500 mg, 1.00 eq.) was dissolved in thionyl chloride (10 mL) and the reaction was heated to 90 °C for 30 min. Upon completion of the reaction, the excess thionyl chloride was removed by concentration under reduced pressure. The residue was cooled to 0 °C and ammonium hydroxide solution (20 mL) was slowly added. The reaction mixture was extracted with dichloromethane (20 mL x 3), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to give 320 mg of 2-chloropyrimidine-4-carboxamide as a white solid. The product was analyzed by LC-MS (electrospray ionization, m/z): 158 [M+H]+.

References

[1] Patent: WO2015/25026, 2015, A1. Location in patent: Page/Page column 209

2-CHLOROPYRIMIDINE-4-CARBOXAMIDESupplier

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