4-CHLORO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER Chemical Properties

Boiling point:

278.2±20.0 °C(Predicted)

Density 

1.311±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

-1.62±0.16(Predicted)

form 

semi-solid

color 

Yellow

InChI

InChI=1S/C7H7ClN2O2/c1-2-12-7(11)5-3-9-4-10-6(5)8/h3-4H,2H2,1H3

InChIKey

AZJAMMCCAZZXIK-UHFFFAOYSA-N

SMILES

C1=NC=C(C(OCC)=O)C(Cl)=N1

Safety Information

HS Code 

2933599590

4-CHLORO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Uses

Ethyl 4-Chloro-5-pyrimidinecarboxylate is a reagent used in the synthesis of a series of novel orally active non-peptide angiotensin II antagonists.

Synthesis

Ethyl 4-hydroxy-5-pyrimidinecarboxylate (380 mg, 2.26 mmol) was dissolved in tetrahydrofuran (THF, 5 mL) and thionyl chloride (1.65 mL, 22.6 mmol) was added slowly. The reaction mixture was heated to reflux and kept for 4 hours. Upon completion of the reaction, the reaction solution was concentrated by rotary evaporator under reduced pressure to give 417 mg (99% yield) of ethyl 4-chloropyrimidine-5-carboxylate as crude product. The crude product could be used directly in the subsequent reaction without further purification or characterization.

References

[1] Patent: WO2006/91506, 2006, A2. Location in patent: Page/Page column 40
[2] Patent: WO2006/49681, 2006, A2. Location in patent: Page/Page column 38
[3] Patent: WO2006/121588, 2006, A2. Location in patent: Page/Page column 44
[4] Patent: WO2006/121860, 2006, A2. Location in patent: Page/Page column 44
[5] Patent: WO2006/121904, 2006, A1. Location in patent: Page/Page column 44

4-CHLORO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER(41103-17-7)Related Product Information

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