Methanol → (8E)-8-[(2Z)-2-(3-hydroxy-4-oxo-1-cyclohexa-2,5-dienylidene)ethylidene ]-7-methyl-1,3-dipropyl-9H-purine-2,6-dione

HRID 375333Notes

Reaction equation

HRID 375333 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29]C)/[CH:6]=[CH:7]/[C:8]1[N:16]([CH3:17])[C:15]2[C:14](=[O:18])[N:13]([CH2:19][CH2:20][CH3:21])[C:12](=[O:22])[N:11]([CH2:23][CH2:24][CH3:25])[C:10]=2[N:9]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[OH:29])/[CH:6]=[CH:7]/[C:8]1[N:16]([CH3:17])[C:15]2[C:14](=[O:18])[N:13]([CH2:19][CH2:20][CH3:21])[C:12](=[O:22])[N:11]([CH2:23][CH2:24][CH3:25])[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 6448585141807-96-7

Product 1

HCID 135665338(8E)-8-[(2Z)-2-(3-hydroxy-4-oxo-1-cyclohexa-2,5-dienylidene)ethylidene ]-7-methyl-1,3-dipropyl-9H-purine-2,6-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 1 (770 mg, 1.87 mmol) obtained in Reference Example 1 was dissolved in 15 ml of methylene chloride. To the solution was added 5.6 ml (5.6 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 purified by silica gel column chromatography to give 550 mg (yield 77%) of Compound 53 as a yellow solid, which was then triturated with ether to give a yellow powder.

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 purified by silica gel column chromatography

Sources & evidence

ORD record
ord-41856875a9be4825b395e9fa0010cddc
Source dataset
uspto-grants-1996_01
Patent number
US05484920

Reaction notes

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