4-AMINO-6-CHLOROPYRIMIDINE-5-CARBONITRILE Chemical Properties

Melting point:

200℃ (DEC.)

Boiling point:

402.4±45.0 °C(Predicted)

Density 

1.53

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

-0.58±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C5H3ClN4/c6-4-3(1-7)5(8)10-2-9-4/h2H,(H2,8,9,10)

InChIKey

MAVMFCKRFRCMLE-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C(C#N)C(N)=N1

Safety Information

HS Code 

2933599590

4-AMINO-6-CHLOROPYRIMIDINE-5-CARBONITRILE Usage And Synthesis

Uses

4-Amino-6-chloropyrimidine-5-carbonitrile is a useful research reagent for organic synthesis and other chemical processes.

Synthesis

The general procedure for the synthesis of 4-amino-6-chloropyrimidine-5-carbonitrile using 4,6-dichloropyrimidine-5-carbonitrile as starting material was as follows: 4,6-dichloropyrimidine-5-carbonitrile (4.8 g, 27.59 mmol) was suspended in 30 mL of dioxane and the mixture was cooled to 0 °C in an ice bath. A methanol solution of ammonia (7 N, 20 mL, 140 mmol) was added slowly and dropwise over a period of 20 minutes. After the dropwise addition, the reaction mixture was continued to be stirred at 0 °C for 30 min. After completion of the reaction, the solvent was removed by rotary evaporator. The crude product was redissolved in tetrahydrofuran, at which point a precipitate was generated, and the precipitate was collected by filtration and washed with additional tetrahydrofuran. The organic solvent was again removed under reduced pressure by rotary evaporator. Finally, the residue was purified using the SP1 purification system (eluent: 20%-80% hexane-ethyl acetate gradient) to afford 2.38 g (56% yield) of the target compound, 4-amino-6-chloropyrimidine-5-carbonitrile, as a white solid with 100% purity.LRMS (m/z): 155 (M + 1)+.

References

[1] Patent: WO2014/60432, 2014, A1. Location in patent: Page/Page column 159
[2] Patent: WO2010/151735, 2010, A2. Location in patent: Page/Page column 57
[3] Patent: US2011/152296, 2011, A1. Location in patent: Page/Page column 15
[4] Patent: US2011/245257, 2011, A1. Location in patent: Page/Page column 15
[5] Patent: WO2012/68343, 2012, A1. Location in patent: Page/Page column 29

4-AMINO-6-CHLOROPYRIMIDINE-5-CARBONITRILE(60025-09-4)Related Product Information

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