Bromine → HCID 18438040, compound

HRID 457372Notes

Reaction equation

HRID 457372 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:17])=[N:7][CH:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[Br:18]Br>CC(O)=O>[Br:18][CH2:17][C:6]1[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 18438119HCID 18438119, compound

Product 1

HCID 18438040HCID 18438040, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-butyl-4-methyl-6-phenyl-pyrimidine (320 mg, 1.14 mmol) and Br2 (0.08 ml, 1.48 mmol) in AcOH (2 mL) is stirred at 80° C. for 2 hours. After cooling, the solution is concentrated. The residue is then partitioned between Et2O and half saturated aqueous NaHCO3. The layers are separated, and the aqueous layer is reextracted once with Et2O. The combined extracts are dried over Na2SO4 and concentrated. The residue is purified by flash chromatography on silica gel. Elution with 3:1 hexanes-EtOAc affords 4-bromomethyl-5-butyl-6-phenyl-pyrimidine and a small amount of an unidentified impurity. 1H NMR (CDCl3, 300 MHz) δ 9.08 (s, 1H), 7.47 (s, 5H), 4.57 (s, 2H), 2.79–2.74 (m, 2H), 1.52–1.42 (m, 2H), 1.38–1.20 (m, 2H), 0.80 (t, J=7.4 Hz, 3H) ppm.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution is concentrated
  3. customThe residue is then partitioned between Et2O and half saturated aqueous NaHCO3
  4. customThe layers are separated
  5. dry with materialThe combined extracts are dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography on silica gel
  8. washElution with 3:1 hexanes-EtOAc

Sources & evidence

ORD record
ord-50831a6df94c4373a302dae59fba8696
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

Loading…