Dichloromethane → 3-Bromo-5-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol

HRID 1614976Notes

Reaction equation

HRID 1614976 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([O:28]C)[CH:27]=1)[CH2:5][NH:6][C:7]1[C:12]([Cl:13])=[CH:11][N:10]=[C:9]([NH:14][C:15]2[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23]O)[CH:18]=[CH:19][CH:20]=2)[N:8]=1.C(Cl)Cl.B(Br)(Br)[Br:34].C([O-])(O)=O.[Na+]>C(=O)=O>[Br:1][C:2]1[CH:27]=[C:26]([OH:28])[CH:25]=[C:4]([CH2:5][NH:6][C:7]2[C:12]([Cl:13])=[CH:11][N:10]=[C:9]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][CH2:23][Br:34])[CH:16]=3)[N:8]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 584678493-[3-({4-[(3-Bromo-5-methoxybenzyl)amino]-5-chloropyrimidin-2-yl}amino)phenyl]propan-1-ol

Product 1

HCID 584679133-Bromo-5-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenolYield 100%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Into a reaction flask was added 3-[3-({4-[(3-bromo-5-methoxybenzyl)amino]-5-chloropyrimidin-2-yl}amino)phenyl]propan-1-ol (2.70 g, 5.65 mmol), methylene chloride (30 mL), and a solution of boron tribromide in methylene chloride (17.0 mL, 17.0 mmol, 1.0 M). The mixture was stirred at rt overnight. The resultant mixture was cooled in dry ice when NaHCO3 (saturated aqueous solution) was added. After removal of the organic solvent, the aqueous layer was extracted with methylene chloride twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated to give the desired product (2.97 g, 100%). LCMS for C20H19Br2ClN4O (M+H)+: m/z=526.9, 528.8.

Workup

  1. additionwas added
  2. customAfter removal of the organic solvent
  3. extractionthe aqueous layer was extracted with methylene chloride twice
  4. washThe combined organic layers were washed with water and brine successively
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5e822ecfee594220a60729c7542c75fd
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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