Boron tribromide → HCID 15953862, compound

HRID 491488Notes

Reaction equation

HRID 491488 reaction equation
[CH:1]([C:4]1[CH:18]=[C:17]([O:19]C)[C:16]([C:21]#[C:22][Si](C)(C)C)=[CH:15][C:5]=1[O:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1)([CH3:3])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:13][C:10]1[N:9]=[C:8]([NH2:14])[C:7]([O:6][C:5]2[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:18][C:17]([OH:19])=[C:16]([C:21]#[CH:22])[CH:15]=2)=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57678393HCID 57678393, compound

Product 1

HCID 15953862HCID 15953862, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2-Isopropyl-4-methoxy-5-trimethylsilanylethynyl-phenoxy)-pyrimidine-2,4-diamine (0.65 g, 1.75 mmol) was added to 40 mL methylene chloride at ice bath temperature and under nitrogen. Boron tribromide (7 mL) was added and the reaction mixture was stirred at ice bath temperature for 1.5 hours, and then for 20 hours at room temperature. The reaction mixture was added to saturated aqueous NaHCO3, and the resulting mixture was extracted with chloroform. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on 50 g of flash silica (2%-6% MeOH/CH2Cl2) to give 103 mg of 4-(2,4-diamino-pyrimidin-5-yloxy)-2-ethynyl-5-isopropyl-phenol, MS (M+H)=285.

Workup

  1. waitfor 20 hours at room temperature
  2. extractionthe resulting mixture was extracted with chloroform
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on 50 g of flash silica (2%-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9b45cc05ec6f4e76939b08a721c8590a
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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