Triethylamine → (2S)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

HRID 420691Notes

Reaction equation

HRID 420691 reaction equation
[CH3:1][C:2]([Si:5]([CH3:25])([CH3:24])[O:6][CH2:7][C@@H:8]([N:11]1[C:16](=[O:17])[CH:15]=[N:14][C:13]2[CH:18]=[CH:19][C:20]([O:22]C)=[N:21][C:12]1=2)[CH2:9]O)([CH3:4])[CH3:3].CCN(CC)CC.CS(OS(C)(=O)=O)(=O)=O>C(Cl)(Cl)Cl.O>[CH3:3][C:2]([Si:5]([CH3:24])([CH3:25])[O:6][CH2:7][C@H:8]1[N:11]2[C:12]3[N:21]([C:20](=[O:22])[CH:19]=[CH:18][C:13]=3[N:14]=[CH:15][C:16]2=[O:17])[CH2:9]1)([CH3:1])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 666584284-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 58001742(2S)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dioneYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one (1 g, 2.74 mmol) in CHCl3 (50 mL) was added Et3N (0.953 mL, 6.84 mmol) followed by a solution of methanesulfonic anhydride (0.953 g, 5.47 mmol) in CHCl3 (50 mL). The reaction mixture was stirred at reflux temperature for 5 h. The crude of reaction was diluted with water, washed with NaCl, dried (MgSO4), filtered, and concentrated. Purification by flash chromatography using a 40 g silica gel cartridge, and mixtures of DCM and MeOH as eluent afforded (2S)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (0.806 g, 88%) as a tan solid.

Workup

  1. temperatureat reflux temperature for 5 h
  2. customThe crude of reaction
  3. washwashed with NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-d2bf43bd85af4a8ea4bbe5ee8a547e1c
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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