5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE Chemical Properties

Boiling point:

451.0±55.0 °C(Predicted)

Density 

1.414±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

3.46±0.42(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C13H19BrN4O2/c1-13(2,3)20-12(19)18-6-4-17(5-7-18)11-15-8-10(14)9-16-11/h8-9H,4-7H2,1-3H3

InChIKey

UKCBGXCNXOKVTF-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCN(C2=NC=C(Br)C=N2)CC1

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

HS Code 

2933599590

5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE Usage And Synthesis

Synthesis

To 1,4-dioxane (30 mL) was added N-BOC-piperazine (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol). The reaction mixture was heated to 110 °C and stirred for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered to remove insoluble material and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (20:1, v/v) to afford tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate as a light yellow solid (3.15 g, 88.7% yield). Mass spectrum (ESI, positive ion mode) m/z: 343.1 [M + H]+. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.29 (s, 2H), 3.83-3.66 (m, 4H), 3.56-3.41 (m, 4H), 1.48 (s, 9H).

References

[1] Patent: WO2016/192657, 2016, A1. Location in patent: Page/Page column 50
[2] Patent: WO2014/131855, 2014, A1. Location in patent: Page/Page column 54; 55
[3] Patent: WO2016/20307, 2016, A1. Location in patent: Page/Page column 44
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8967 - 9004
[5] Patent: WO2017/144633, 2017, A1. Location in patent: Page/Page column 109

5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE(374930-88-8)Related Product Information

• tert-butyl 4-(5-iodopyrimidin-2-yl)piperazine-1-carboxylate
• tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate
• 5-BROMO-2-(4-METHYLPIPERAZIN-1-YL)PYRIMIDINE
• 5-BROMO-2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE
• N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINE