Bromine → HCID 18438040, compound

HRID 1643205Notes

Reaction equation

HRID 1643205 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=7.41Hz, 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-23fff3c33c794a27a4f8f5dd7b49b4a9
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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