Water → HCID 15432863, compound

HRID 2297599Notes

Reaction equation

HRID 2297599 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([N:17]1[C:21]2[C:22](=[O:33])[N:23]([CH2:31][CH3:32])[C:24]3[N:25]([N:26]=[C:27]([CH2:29]Br)[N:28]=3)[C:20]=2[N:19]=[C:18]1[CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CN(C)C=O>[CH2:10]([N:17]1[C:21]2[C:22](=[O:33])[N:23]([CH2:31][CH3:32])[C:24]3[N:25]([N:26]=[C:27]([CH2:29][O:9][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[N:28]=3)[C:20]=2[N:19]=[C:18]1[CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 15432862HCID 15432862, compound

Product 1

HCID 15432863HCID 15432863, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

66 mg of sodium hydride (66% in mineral oil) are added to a solution of 0.16 g of phenol in 15 ml of dimethylformamide. After 30 minutes' stirring at ambient temperature, 0.68 g of 6-benzyl-2-bromomethyl-7-cyclopentyl-4-ethyl-imidazo[4,5-e]-s-triazolo[1,5-a]pyrimidin-5-one are added. The mixture is stirred at elevated temperature (about 100° C.) until the reaction is complete (about 8 hours). For working up, some water is added and then the solvent is distilled off in vacuo. The residue remaining is taken up in 20 ml of dichloromethane and 20 ml of water. After acidification with aqueous 1N HCl solution, the organic phase is separated off, washed with water and dried over magnesium sulphate. The solvent is distilled off and the residue remaining is recrystallised from diethyl ether. 0.6 g of the title compound remain, pure enough to be used in the subsequent reactions.

Workup

  1. stirringThe mixture is stirred at elevated temperature (about 100° C.) until the reaction
  2. custom(about 8 hours)
  3. distillationthe solvent is distilled off in vacuo
  4. customAfter acidification with aqueous 1N HCl solution, the organic phase is separated off
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. distillationThe solvent is distilled off
  8. customthe residue remaining is recrystallised from diethyl ether

Sources & evidence

ORD record
ord-6abdaa1fdd8e4055a8329a8c0389fc31
Source dataset
uspto-grants-2002_12
Patent number
US06492377B1

Reaction notes

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