Boron tribromide → HCID 18323737, compound

HRID 1872041Notes

Reaction equation

HRID 1872041 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10]C)[C:3]=1[N:12]([CH2:21][CH3:22])[C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[N:14]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([OH:10])[C:3]=1[N:12]([CH2:21][CH3:22])[C:13]1[N:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[N:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9907170HCID 9907170, compound

Product 1

HCID 18323737HCID 18323737, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-Bromo-4,6-dimethoxyphenyl)-N-ethyl-4,6-dimethyl-2-pyrimidinamine (214 mg, 0.58 mmol) in 15 mL dichloromethane under nitrogen was cooled in a dry ice/acetone bath, and boron tribromide (1.0 M in dichloromethane, 0.58 mL) was slowly added. The reaction was allowed gradually to warm to room temperature whereupon it was stirred overnight. After quenching with water, the aqueous portion was basified with saturated sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried with magnesium sulfate and concentrated in vacuo to give a tan solid. The solid was recrystallized form ethyl acetate/hexanes to yield 58 mg product; mp 157-160° C. Anal. Calcd. %C: 51.15: %H: 5.15: %N: 11.93: %Br: 22.69. Found %C: 51.02: %H: 5.10: %N: 11.83: %Br: 22.52.

Workup

  1. customAfter quenching with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a tan solid
  6. customThe solid was recrystallized form ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b00ae9310ca84aa9b68666b1b641318e
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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