Hydrogen Peroxide → HCID 22226526, compound

HRID 896058Notes

Reaction equation

HRID 896058 reaction equation
Cl.[CH2:2]([N:5]1[C:13]2[N:12]=[C:11]([CH2:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=4)[CH:18]=[N:17][CH:16]=3)[NH:10][C:9]=2[C:8](=[O:29])[N:7]([CH3:30])[C:6]1=[O:31])[CH:3]=[CH2:4].C(N(C(C)C)CC)(C)C.[OH-:41].[Na+].OO>C1COCC1>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[CH:18]=[N:17][CH:16]=[C:15]2[CH2:14][C:11]1[NH:10][C:9]2[C:8](=[O:29])[N:7]([CH3:30])[C:6](=[O:31])[N:5]([CH2:2][CH2:3][CH2:4][OH:41])[C:13]=2[N:12]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 22226559HCID 22226559, compound

Product 1

HCID 22226526HCID 22226526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of the product of Example 13, 3-allyl-8-(6,7-dimethoxy-isoquinolin4-ylmethyl)-1-methyl-3,7-dihydro-purine-2,6-dione hydrochloride salt (0.760 g, 1.87 mmol), 9-borabicyclo[2.2.0]nonane (0.5M THF solution, 18.7 ml, 9.35 mmol) and diisopropylethylamine (0.33 ml, 1.89 mmol) in THF (9 ml) is heated to reflux for 2.5 hours. Sodium hydroxide (4M aqueous solution, 6 ml) and hydrogen peroxide (27.5%, 3 ml) are added sequentially and the reaction heated at 50° C. for 1.5 hours. After evaporation, the crude product is purified by flash chromatography (19:1 CH2Cl2:-methanol elution) and triturated with water to afford 8-(6,7-dimethoxy-isoquinolin4-ylmethyl)-3-(3-hydroxy-propyl)-1-methyl-3,7-dihydro-purine-2,6-dione, [MH]+ 426.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 2.5 hours
  3. customAfter evaporation
  4. customthe crude product is purified by flash chromatography (19:1 CH2Cl2:-methanol elution)
  5. customtriturated with water

Sources & evidence

ORD record
ord-853c16982d8b499689894c7dd88448db
Source dataset
uspto-grants-2005_07
Patent number
US06919337B2

Reaction notes

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