Boron tribromide → HCID 25062427, compound

HRID 1666225Notes

Reaction equation

HRID 1666225 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:19]([CH3:20])[C:18]3[C:17](=[O:21])[N:16]([CH2:22][C:23]#[CH:24])[C:15](=[O:25])[N:14]([CH3:26])[C:13]=3[N:12]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:19]([CH3:20])[C:18]3[C:17](=[O:21])[N:16]([CH2:22][C:23]#[CH:24])[C:15](=[O:25])[N:14]([CH3:26])[C:13]=3[N:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 25062158HCID 25062158, compound

Product 1

HCID 25062427HCID 25062427, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg (0.28 mmol) 8-(3-methoxyphenylethynyl)-3,7-dimethyl-1-prop-2-ynyl-3,7-dihydropurine-2,6-dione in dichloromethane (25 mL) was added boron tribromide (0.5 mL, 5.3 mmol) at room temperature. After a few minutes precipitation of a yellow solid could be observed. The suspension was stirred for 0.5-1 h at room temperature until no starting material could be detected by TLC analyses (eluent: dichloromethane/methanol, 9.5:0.5). After hydrolysis with concentrated NaHCO3 solution (50 mL) the dichloromethane was removed under reduced pressure. The precipitate was filtered under reduced pressure, washed with water, dried at 70° C. and purified by column chromatography on silica gel (eluent: dichloro-methane/methanol, 9.5:0.5 or 9:1): colorless crystals (yield: 76%), m.p. 271° C.

Workup

  1. customAfter a few minutes precipitation of a yellow solid
  2. customAfter hydrolysis with concentrated NaHCO3 solution (50 mL) the dichloromethane
  3. customwas removed under reduced pressure
  4. filtrationThe precipitate was filtered under reduced pressure
  5. washwashed with water
  6. customdried at 70° C.
  7. custompurified by column chromatography on silica gel (eluent: dichloro-methane/methanol, 9.5:0.5 or 9:1)

Sources & evidence

ORD record
ord-d86e02296b5d41d0b76c9f9b5d838d0c
Source dataset
uspto-grants-2011_10
Patent number
US08044061B2

Reaction notes

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