Home Cart Sign in  
Chemical Structure| 4595-59-9 Chemical Structure| 4595-59-9
Chemical Structure| 4595-59-9

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of 5-Bromopyrimidine

CAS No. :4595-59-9
Formula : C4H3BrN2
M.W : 158.98
SMILES Code : C1=NC=NC=C1Br
MDL No. :MFCD00006117
InChI Key :GYCPLYCTMDTEPU-UHFFFAOYSA-N
Pubchem ID :78344

Safety of 5-Bromopyrimidine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 5-Bromopyrimidine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 4595-59-9 ]
  • Downstream synthetic route of [ 4595-59-9 ]

[ 4595-59-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 110-91-8 ]
  • [ 4595-59-9 ]
  • [ 57356-66-8 ]
References: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1586 - 1605.
  • 2
  • [ 4595-59-9 ]
  • [ 23719-80-4 ]
  • [ 1346697-39-9 ]
YieldReaction ConditionsOperation in experiment
41% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 17 h; 5-Bromopyrimidine (8 g, 50.3 mmol) was taken in anhydrous THF (160 mL) followed by the addition of cyclopropylmagnesium bromide (106 mL, 52.8 mmol, 0.5 M solution in THF) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour, and then treated with a solution of 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (1 1.42 g, 50.3 mmol) in THF (26 mL). The resultant brown mixture was allowed to stir at room temperature for 16 hours and then evaporated under reduced pressure. The brown solid was suspended in water and extracted with dichloromethane (3x50 mL). The combined organics were washed with a IN aqueous solution of sodium hydroxide (2x15 mL), water, and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography using 160 g BIOTAGE.(R). column eluting with hexanes/EtOAc (9: 1) to provide Intermediate 61 as a pale yellow solid (4.1 g, 41 percent yield). MS (ES): m/z=199.05 [M+H]+. Intermediate 61 was used in the synthesis of Example 214.
20% at 0 - 20℃; for 1 h; Inert atmosphere To a solution of 5-bromopyrimidine (3 g, 18.87 mmol) in Et20 (120 mL) and THF (20ml) was added cyclopropylmagnesium bromide (39.6 mL, 19.81 mmol) at 0°C. The resulting white suspension was stirred at rt for lh and quenched with water (0.340 mL, 18.87 mmol) followed by addition of DDQ (4.28 g, 18.87 mmol) in THF (10ml). The resulting black mixture was stirred at room temperature overnight. The reaction mixture was extracted with EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with NaOH (IN) and brine. The crude product was purified by Biotage (0-15percent EtOAc/hexanes, 1.2L) to afford the title compound (700 mg, 20percent) as a yellow solid. XH NMR (500 MHz, CC13D) δ ppm 8.87 (1 H, s), 8.66 (1 H, s), 2.40-2.56 (1 H, m), 1.13-1.32 (4 H, m).
20%
Stage #1: at 0 - 20℃;
Stage #2: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; diethyl ether at 20℃;
Preparation 11 A: 5-Bromo-4-cyclopropylpyrimidine [00148] To a solution of 5-bromopyrimidine (3 g, 18.87 mmol) in Et20 (120 mL) and THF (20ml) was added cyclopropylmagnesium bromide (39.6 mL, 19.81 mmol) at 0 °C. The resulting white suspension was stirred at room temperature for lh and quenched with water (0.340 mL, 18.87 mmol) followed by addition of DDQ (4.28 g, 18.87 mmol) inTHF (10ml). The resulting black mixture was stirred at room temperature overnight. The reaction mixture was extracted with EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with NaOH (IN) and brine. The crude product was purified by BIOTAGE® (0-15percent EtOAc/hexanes, 1.2L) to afford the title compound (700 mg, 20percent) as a yellow solid. XH NMR (500 MHz, chloroform-d) δ ppm 8.87 (1 hr, s), 8.66 (1 hr, s), 2.40-2.56 (1 hr, m), 1.13-1.32 (4 hr, m).
References: [1] Patent: WO2012/15723, 2012, A1, . Location in patent: Page/Page column 107; 108.
[2] Patent: WO2012/9510, 2012, A1, . Location in patent: Page/Page column 54; 55.
[3] Patent: WO2013/49263, 2013, A1, . Location in patent: Paragraph 00147; 00148.
 

Historical Records

Technical Information

Categories