4-(6-Chloro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester Chemical Properties

Boiling point:

437.3±45.0 °C(Predicted)

Density 

1.253

storage temp. 

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

pka

3.29±0.26(Predicted)

4-(6-Chloro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester Usage And Synthesis

Synthesis

Step 1: Synthesis of tert-butyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylate In a microwave reaction tube, 4,6-dichloropyrimidine (0.5 g, 3.36 mmol), N-BOC-piperazine (0.69 g, 3.36 mmol) and triethylamine (0.34 g, 3.36 mmol) were dissolved in acetonitrile (10 mL). The reaction mixture was microwaved at 120 °C for 2 hours. After completion of the reaction, the mixture was diluted with ethyl acetate, washed sequentially with saturated ammonium chloride solution and dried over anhydrous magnesium sulfate. The drier was removed by filtration and the filtrate was concentrated under reduced pressure to afford the target compound tert-butyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylate (0.82 g, 91% yield). 1H NMR (500MHz, CDCl3): δ 8.39 (s, 1H), 6.50 (s, 1H), 3.65 (m, 4H), 3.52 (m, 4H), 1.48 (s, 9H).

References

[1] Patent: WO2012/69852, 2012, A1. Location in patent: Page/Page column 69
[2] Patent: CN106045918, 2016, A. Location in patent: Paragraph 0098; 0099
[3] Patent: US2009/163508, 2009, A1. Location in patent: Page/Page column 21
[4] Patent: WO2007/56023, 2007, A2. Location in patent: Page/Page column 57
[5] Patent: US2009/163508, 2009, A1. Location in patent: Page/Page column 36

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