Boron tribromide → HCID 178503592, compound

HRID 411563Notes

Reaction equation

HRID 411563 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27]C)[CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([S:29][CH3:30])[NH:11]1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([S:29][CH3:30])[NH:11]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178490014HCID 178490014, compound

Product 1

HCID 178503592HCID 178503592, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 55 mg (0.11 mmol) of 1-(2,4,6-trichlorophenyl)-3-(methylthio)-6-(3-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one in 2 mL of CH2Cl2 was added 1 mL (1 mmol) of 1 M boron tribromide in CH2Cl2. The solution was stirred 35 min. at ambient temperature, and it was then cooled to 0° C. The reaction was quenched with 4 mL of 1 M aq. HCl. The mixture was poured into water and extracted with EtOAc. The organic extract was washed with brine, dried (MgSO4), and concentrated under reduced pressure to afford 52 mg (98%) of 1-(2,4,6-trichlorophenyl)-3-(methylthio)-6-(3-hydroxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one as an off-white solid, m.p. 264-266° C. Mass spec. Calc'd for C19H13N4O2SCl3: 465.9825(M)+. Found: 465.9798.

Workup

  1. temperatureit was then cooled to 0° C
  2. customThe reaction was quenched with 4 mL of 1 M aq. HCl
  3. additionThe mixture was poured into water
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2874d3df9b604e32818a4bf5e42d35fe
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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