Bromine → HCID 18438039, compound

HRID 457377Notes

Reaction equation

HRID 457377 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:18])=[N:7][C:8]([Cl:17])=[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:19]Br>CC(O)=O>[Br:19][CH2:18][C:6]1[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:9]=[C:8]([Cl:17])[N:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 18438114HCID 18438114, compound

Product 1

HCID 18438039HCID 18438039, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the 5-butyl-2-chloro-4-methyl-6-phenyl-pyrimidine (215 mg, 0.825 mmol) and Br2 (0.042 ml, 0.825 mmol) in AcOH (2 mL) is stirred at 80° C. for 2 hours. After cooling, the solution is concentrated. The residue is 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 to 305 mg of crude 4-bromomethyl-5-butyl-2-chloro-6-phenyl-pyrimidine, which also contains small amounts of SM and dibromo material. This material is used without further purification.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution is concentrated
  3. customThe residue is 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 to 305 mg of crude 4-bromomethyl-5-butyl-2-chloro-6-phenyl-pyrimidine, which also contains small amounts of SM and dibromo material
  7. customThis material is used without further purification

Sources & evidence

ORD record
ord-2d2ab3cff8d2418fa366ac320e901400
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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