HCID 86606996, compound → HCID 86606995, compound

HRID 1868465Notes

Reaction equation

HRID 1868465 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[CH:15]=[C:16]([C:18](=[O:23])N(OC)C)[N:17]=[C:13]2[N:12]=[C:11]([CH3:24])[C:10]=1[CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].[CH3:34][Mg+].[Br-]>C1COCC1>[C:18]([C:16]1[N:17]=[C:13]2[N:12]=[C:11]([CH3:24])[C:10]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:14]2[CH:15]=1)(=[O:23])[CH3:34]

Participants

4

Reactant 2

HCID 86606996HCID 86606996, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 86606995HCID 86606995, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl (5-(2,4-dichlorophenyl)-2-(methoxy(methyl)carbamoyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (intermediate for Example 59, 15 mg, 0.03 mmol) in THF (1 mL) at 0° C. was added MeMgBr (3M in THF, 0.05 mL, 0.15 mmol). After 30 min, the reaction was quenched with satd aq NH4Cl and diluted with EtOAc. The organic layer was washed with satd aq NH4Cl and brine prior to drying over MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded tert-butyl (2-acetyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (10 mg, 73%) as a white solid.

Workup

  1. customthe reaction was quenched with satd aq NH4Cl
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with satd aq NH4Cl and brine
  4. dry with materialto drying over MgSO4
  5. filtrationFiltration, concentration
  6. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-32883d0bfd25442caa8e39caa3977def
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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