Bromine → 4-Bromomethyl-5-propyl-6-chloro-pyrimidine

HRID 898702Notes

Reaction equation

HRID 898702 reaction equation
[Br:1]Br.[Cl:3][C:4]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:8]([CH3:13])[N:7]=[CH:6][N:5]=1>CC(O)=O>[Br:1][CH2:13][C:8]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:4]([Cl:3])[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 223131564-Chloro-6-methyl-5-propylpyrimidine

Product 1

HCID 223131604-Bromomethyl-5-propyl-6-chloro-pyrimidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

Br2 (0.153 ml, 3 mmol) is added dropwise to a solution of 4-chloro-6-methyl-5-propyl-pyrimidine (3 mmol) heated at 85° C. in HOAc (10 ml). After the addition, the mixture is stirred at 85° C. for 1 hour. The solvent is removed in vacuo and the residue dissolved in EtOAc (15 ml), washed with Na2S2O3 solution (sat. 5 ml), followed by NaHCO3 (10 ml), and brine (10 ml). The organic phase is dried (Na2SO4) and evaporated. The resulting yellow oil is purified by flash column chromatography, which provides the title compound.

Workup

  1. additionAfter the addition
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc (15 ml)
  4. washwashed with Na2S2O3 solution (sat. 5 ml)
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. customevaporated
  7. customThe resulting yellow oil is purified by flash column chromatography, which

Sources & evidence

ORD record
ord-de3ee40559ca4a96873748834613235b
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

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