Hydrochloric Acid → HCID 59310118, compound

HRID 1513064Notes

Reaction equation

HRID 1513064 reaction equation
[Cl:1][C:2]1[C:7](OC=C=O)=[C:6]([O:12][CH3:13])[C:5]([O:14][CH2:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]([F:24])[C:17]=2[F:25])=[CH:4][C:3]=1[N:26]1[C:34](=[O:35])[NH:33][C:32]2[C:27]1=[N:28][C:29]([CH3:38])=[N:30][C:31]=2[O:36][CH3:37].C[Mg]Br.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:12][CH2:13][C:6]([OH:12])([CH3:7])[CH3:5])[C:5]([O:14][CH2:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]([F:24])[C:17]=2[F:25])=[CH:4][C:3]=1[N:26]1[C:34](=[O:35])[NH:33][C:32]2[C:27]1=[N:28][C:29]([CH3:38])=[N:30][C:31]=2[O:36][CH3:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86641285HCID 86641285, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59310118HCID 59310118, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxy-carbonylmethoxyphenyl]-6-methoxy-2-methyl-7,9-dihydro-8H-purin-8-one (34 mg) in tetrahydrofuran (3 mL) was added methylmagnesium bromide (1 mol/L tetrahydrofuran solution, 031 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/4) to give the title compound (4 mg).

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/4)

Sources & evidence

ORD record
ord-ce2f2e7017124a308c7bbce38719fac3
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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