tert-Butyldimethylsilyl trifluoromethanesulphonate → HCID 86690365, compound

HRID 1183145Notes

Reaction equation

HRID 1183145 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[N:8]=[CH:7][N:6]([C@H:16]1[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]1[OH:22])[C:5]2=[O:23].[CH3:24][C:25]([Si:28](OS(C(F)(F)F)(=O)=O)([CH3:30])[CH3:29])([CH3:27])[CH3:26].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[N:8]=[CH:7][N:6]([C@H:16]1[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]1[O:22][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29])[C:5]2=[O:23]

Participants

6

Reactant 3

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 699279036-bromo-3-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]benzo[h]quinazolin-4(3H)-one

Product 1

HCID 86690365HCID 86690365, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-3-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]benzo[h]quinazolin-4(3H)-one (1.00 g, 2.67 mmol) in CH2Cl2 (40 mL) was added DMAP (1.68 g, 13.3 mmol) and then tert-butyl dimethylsilyl trifluoromethane sulfonate (1.84 mL, 8.00 mmol) and the reaction was stirred overnight. The reaction was diluted with saturated, aqueous NaHCO3 and extracted 1× with CH2Cl2. The organics were washed with brine, dried over MgSO4, filtered, concentrated, and dried. The oily residue was purified via silica gel chromatography, eluting with 5-55% ethyl acetate in hexanes to provide 1,5-anhydro-3-(6-bromo-4-oxobenzo quinazolin-3(4H)-yl)-2-O-[tert-butyl(dimethyl)silyl]-3,4-dideoxy-L-threo-pentitol that gave a mass ion (ES+) of 490.8 for [M+H]+.

Workup

  1. extractionextracted 1× with CH2Cl2
  2. washThe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried
  7. customThe oily residue was purified via silica gel chromatography
  8. washeluting with 5-55% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3cd387651afd4c289d3c527f4a8d5b6b
Source dataset
uspto-grants-2014_03
Patent number
US08664234B2

Reaction notes

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