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

HRID 916636Notes

Reaction equation

HRID 916636 reaction equation
[Br:1]Br.[CH2:3]([C:6]1[C:7]([Cl:13])=[N:8][CH:9]=[N:10][C:11]=1[CH3:12])[CH2:4][CH3:5]>CC(O)=O>[CH2:3]([C:6]1[C:7]([Cl:13])=[N:8][CH:9]=[N:10][C:11]=1[CH2:12][Br:1])[CH2:4][CH3:5]

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 (1.28 g, 8 mmol) is added dropwise to a stirred solution 101 in HOAc (20 ml) heated at 85° C. After addition, the mixture is stirred at 85° C. for 1 hour. The solvent is removed in vacuo and EtOAc (25 ml) and NaHCO3 (25 ml) are added to the residue. The layers are separated and the organic layer is washed with Na2S2O3 solution (sat. 15 ml) followed by brine (20 ml). The organic phase is dried (Na2SO4) and evaporated. The resulting yellow oil is purified by flash column (6:1 EtOAc, hexane) to afford the product (102) as a light yellow solid.

Workup

  1. additionAfter addition
  2. customThe solvent is removed in vacuo and EtOAc (25 ml) and NaHCO3 (25 ml)
  3. additionare added to the residue
  4. customThe layers are separated
  5. washthe organic layer is washed with Na2S2O3 solution (sat. 15 ml)
  6. dry with materialThe organic phase is dried (Na2SO4)
  7. customevaporated
  8. customThe resulting yellow oil is purified by flash column (6:1 EtOAc, hexane)

Sources & evidence

ORD record
ord-67ae873481174f1e89bb9b2cdb9646f3
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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