HCID 67192531, compound → HCID 67192793, compound

HRID 2401310Notes

Reaction equation

HRID 2401310 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[O:7][C:8]1[N:9]([CH2:23][CH2:24][CH3:25])[C:10](=[O:22])[C:11]2[NH:12][C:13]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:14][C:15]=2[N:16]=1)(=[O:3])[CH3:2].[CH3:29][Mg]Br>C1COCC1>[CH:17]1([C:13]2[NH:12][C:11]3[C:10](=[O:22])[N:9]([CH2:23][CH2:24][CH3:25])[C:8]([O:7][C:6]4[CH:26]=[CH:27][CH:28]=[C:4]([C:1]([OH:3])([CH3:29])[CH3:2])[CH:5]=4)=[N:16][C:15]=3[N:14]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 67192531HCID 67192531, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 67192793HCID 67192793, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Acetyl-phenoxy)-8-cyclopentyl-1-propyl-1,7-dihydro-purin-6-one (0.08 g, 0.21 mmol), was taken in THF. To this was added methyl magnesium bromide (30 μl, 0.25 mmol) drop wise at −70° C. and stirred for 2 hours. Another lot of methyl magnesium bromide (30 μl, 0.25 mmol) was added and stirred further for 2 hours. Reaction was quenched with saturated NH4Cl solution and concentrated to evaporate THF and residue was dissolved in ethyl acetate, washed with water followed by brine and dried over anhydrous Na2SO4. The crude product was purified by preparative TLC to give the product (0.027 g) as an off white solid in 32% yield.

Workup

  1. stirringstirred further for 2 hours
  2. customReaction
  3. customwas quenched with saturated NH4Cl solution
  4. concentrationconcentrated
  5. customto evaporate THF and residue
  6. dissolutionwas dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-8c5e3572aedb4ba8bd38c0932dc01850
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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