Methanol → 1H-Purine-2,6-dione,8-[2-(3,4-dihydroxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-7-methyl-, (E)-(9CI)

HRID 1081843Notes

Reaction equation

HRID 1081843 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27]C)/[CH:6]=[CH:7]/[C:8]1[N:16]([CH3:17])[C:15]2[C:14](=[O:18])[N:13]([CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH3:23])[C:10]=2[N:9]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[OH:27])/[CH:6]=[CH:7]/[C:8]1[N:16]([CH3:17])[C:15]2[C:14](=[O:18])[N:13]([CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH3:23])[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 5311037Istradefylline

Product 1

HCID 1357703381H-Purine-2,6-dione,8-[2-(3,4-dihydroxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-7-methyl-, (E)-(9CI)Yield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 65 (2.00 g, 5.20 mmol) obtained in Example 8 was dissolved in 40 ml of methylene chloride. To the solution was added 26 ml (26 mmol) of boron tribromide (1.0M methylene chloride solution) under ice cooling in argon atmosphere, and the mixture was stirred overnight at room temperature. Methanol was added thereto and the mixture was separated with chloroform-an aqueous solution of sodium bicarbonate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was recrystallized from ethanol to give 643 mg (yield 35%) of Compound 173 as pale yellow grains.

Workup

  1. customthe mixture was separated with chloroform-an aqueous solution of sodium bicarbonate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customfollowed by evaporation under reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-55002bedc4c9477782cd9a9f34c5446c
Source dataset
uspto-grants-1996_12
Patent number
US05587378

Reaction notes

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