| Identification | Back Directory | [Name]
5-Bromo-2-cyclopropylpyrimidine | [CAS]
304902-96-3 | [Synonyms]
2-Cyclopropyl-5-bromopyrimidine
5-Bromo-2-cyclopropylpyrimidine
Pyrimidine, 5-bromo-2-cyclopropyl-
5-bromo-2-cyclopropylpyrimidine-4,6-d2
5-Bromo-2-cyclopropylpyrimidine ISO 9001：2015 REACH | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C7H7BrN2 | [MDL Number]
MFCD14702784 | [MOL File]
304902-96-3.mol | [Molecular Weight]
199.05 |
| Chemical Properties | Back Directory | [Boiling point ]
255℃ | [density ]
1.657 | [Fp ]
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 |
| Hazard Information | Back Directory | [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 |
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