反应 #470439

ord-d3a42bce36734cdfa320fdae2d93aa99

反应方程式

CCC(=N)N.Cl
propionimidamide hydrochloride
CC[O-].[Na+]
sodium ethoxide
O=C/C(Br)=C(/Br)C(=O)O
mucobromic acid
CC[O-].[Na+]
sodium ethoxide
[Na]
Sodium
CCc1ncc(Br)c(C(=O)O)n1
5-Bromo-2-ethylpyrimidine-4-carboxylic acid
收率 37.0%

反应条件

温度
55°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他the heating bath was removed
  2. 2
    温度maintained a constant temperature
  3. 3
    温度After cooling
  4. 4
    过滤the mixture was filtered
  5. 5
    其他evaporated to a residue which
  6. 6
    过滤The brown precipitate was filtered off
  7. 7
    洗涤washed with cold water
  8. 8
    其他freeze-dried

实验过程

Sodium (356 mg, 15.5 mmol) was carefully added to ethanol (5.9 mL) to prepare sodium ethoxide solution in ethanol. The above freshly prepared ethanol solution (3.5 mL) was added to a stirred suspension of propionimidamide hydrochloride (1.05 g, 9.69 mmol). The mixture was warmed to 55° C., then the heating bath was removed and a solution of mucobromic acid (1 g, 3.87 mmol) in ethanol was added dropwise at a rate which maintained a constant temperature, followed by a further sodium ethoxide solution (2 mL). After cooling, the mixture was filtered and evaporated to a residue which was shaken vigorously with hydrochloric acid (2 M×2.4 mL). The brown precipitate was filtered off and washed with cold water, then freeze-dried to give 5-Bromo-2-ethylpyrimidine-4-carboxylic acid (330 mg, 37%) as a yellow solid. LCMS: 231 [M+1]+, 1H NMR (400 MHz, DMSO-d6): δ 1.25 (t, J=7.6 Hz, 3H), 2.88 (q, J=7.6 Hz, 2H), 9.05 (s, 1H).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08367663B2uspto-grants-2013_02