Water → HCID 178437544, compound

HRID 892117Notes

Reaction equation

HRID 892117 reaction equation
[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:14][C:15]=3[N:16]=[C:17]2Cl)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([Mg]Br)[CH3:27].O.C(OCC)(=O)C>O1CCCC1>[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:14][C:15]=3[N:16]=[C:17]2[CH2:26][CH3:27])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 178418443HCID 178418443, compoundHCID 178478320(8R)-8-benzyl-5-chloro-2-cyclopentyl-7,8-dihydro-1H-imidazo[2,1-f]purine

Product 1

HCID 178437544HCID 178437544, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Compound 67a (82 mg, 0.20 mmol) obtained in Example 67 was dissolved in tetrahydrofuran (1 mL), to the solution was added a 1 mol/L solution (2 mL) of ethyl magnesium bromide in tetrahydrofuran, and the mixture was stirred at 60° C. for 1 hour. To the reaction mixture was added water and the mixture was stirred. Ethyl acetate was added to the mixture and the organic layer was washed with water and dried over magnesium sulfate. The organic layer was concentrated and to the residue were added dichloromethane and diisopropyl ether. The deposited crystals were collected by filtration to obtain the title compound (40 mg, 58%) as a white solid.

Workup

  1. stirringthe mixture was stirred
  2. washthe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic layer was concentrated and to the residue
  5. additionwere added dichloromethane and diisopropyl ether
  6. filtrationThe deposited crystals were collected by filtration

Sources & evidence

ORD record
ord-ae98f0a75b9f4b9ba79e7eab29862792
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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