5-Bromo-2-cyclopropylpyrimidine Chemical Properties

Boiling point:

255℃

Density 

1.657

Flash point:

108℃

storage temp. 

Store at room temperature

pka

0.67±0.22(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C7H7BrN2/c8-6-3-9-7(10-4-6)5-1-2-5/h3-5H,1-2H2

InChIKey

ANURJXNEVQWODA-UHFFFAOYSA-N

SMILES

C1(C2CC2)=NC=C(Br)C=N1

Safety Information

HS Code 

2933599590

5-Bromo-2-cyclopropylpyrimidine Usage And Synthesis

Uses

5-?Bromo-?2-?cyclopropylpyrimidin?e is a reagent used in the synthesis of novel glucocorticoid modulators which are used in the treatment of inflammatory diseases.

Synthesis

5-Bromo-2-iodopyrimidine (5.00 g, 17.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (5.70 mg, 5.00 mmol) were dissolved in tetrahydrofuran (80 mL). Cyclopropylmagnesium bromide (0.5 mol/L in THF, 70.0 mL, 35.0 mmol) was added slowly and dropwise under nitrogen protection. The reaction mixture was stirred at 70 °C for 2 hours. After completion of the reaction, the reaction solution was diluted with water (20 mL) and subsequently extracted with ethyl acetate (50 mL x 3). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 50:1) to afford 5-bromo-2-cyclopropylpyrimidine (1.20 g, 35% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.51 (s, 2H), 2.17-2.11 (m, 1H), 1.04-1.02 (m, 4H). Mass spectrum (ESI) showed m/z 199 ([M + H]+).

References

[1] Patent: US2015/51395, 2015, A1. Location in patent: Paragraph 1352-1353