Water → HCID 15432861, compound

HRID 2297597Notes

Reaction equation

HRID 2297597 reaction equation
[CH2:1]([N:8]1[C:12]2[C:13](=[O:33])[N:14]([CH2:31][CH3:32])[C:15]3[N:16]([N:17]=[C:18]([CH2:20][O:21]CC4C=CC(OC)=CC=4)[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[CH2:1]([N:8]1[C:12]2[C:13](=[O:33])[N:14]([CH2:31][CH3:32])[C:15]3[N:16]([N:17]=[C:18]([CH2:20][OH:21])[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15432860HCID 15432860, compound

Product 1

HCID 15432861HCID 15432861, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-benzyl-7-cyclopentyl-4-ethyl-2-[(4-methoxybenzyloxy)methyl]-imidazo[4,5-e]-s-triazolo[1,5-a]pyrimidin-5-one (1.03 g) is dissolved in 20 ml of dichloromethane and 1.2 ml of water are added. At ambient temperature, 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ, 0.68 g) is added with stirring and the mixture is stirred for a further 4 hours. After the 2,3-dichloro-5,6-dicyanobenzoquinone precipitate has been separated off, the remaining solution is washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and dried over sodium sulphate. The solvent is distilled of and the residue remaining is crystallised from diethyl ether. 0.74 g of 6-benzyl-7-cyclopentyl-4-ethyl-2-hydroxymethyl-imidazo[4,5-e]-s-triazolo[1,5-a]pyrimidin-5-one are obtained in the form of slightly reddish crystals which can be used in the next step without further purification.

Workup

  1. stirringthe mixture is stirred for a further 4 hours
  2. customAfter the 2,3-dichloro-5,6-dicyanobenzoquinone precipitate has been separated off
  3. washthe remaining solution is washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. distillationThe solvent is distilled of and the residue
  6. customremaining is crystallised from diethyl ether

Sources & evidence

ORD record
ord-bc1c3bf82d4940d9b35030b44cdd9c9f
Source dataset
uspto-grants-2002_12
Patent number
US06492377B1

Reaction notes

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