Trimethylsilyl iodide → HCID 178432310, compound

HRID 869705Notes

Reaction equation

HRID 869705 reaction equation
C[O:2][C:3]1[N:4]=[C:5]2[CH2:13][CH2:12][CH2:11][O:10][C:6]2=[N:7][C:8]=1[CH3:9].I[Si](C)(C)C>S1(CCCC1)(=O)=O.C(OCC)(=O)C>[CH3:9][C:8]1[N:7]=[C:6]2[O:10][CH2:11][CH2:12][CH2:13][C:5]2=[N:4][C:3]=1[OH:2]

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67395445HCID 67395445, compound

Product 1

HCID 178432310HCID 178432310, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
42.5 °C

Procedure

To a suspension of 2-methoxy-3-methyl-7,8-dihydro-6H-pyrano[2,3-b]pyrazine (1.95 g, 10.8 mmol) in sulfolane (25 mL) was added iodotrimethylsilane (15.0 g, 75.0 mmol) at 30° C. The reaction mixture was heated at 40-45° C. for 8 h, and then cooled to ambient temperature and stirred for 2 days. And the reaction mixture was diluted with ethyl acetate and washed with 2% aqueous sodium sulfite. The aqueous layer was extracted with ethyl acetate and chloroform. The organic layer was combined, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=93:7) to give 3-methyl-7,8-dihydro-6H-pyrano[2,3-b]pyrazin-2-ol and recovered starting material. MS (APCI): m/z 177 (M+H).

Workup

  1. temperaturecooled to ambient temperature
  2. washwashed with 2% aqueous sodium sulfite
  3. extractionThe aqueous layer was extracted with ethyl acetate and chloroform
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=93:7)

Sources & evidence

ORD record
ord-2728a264f3294845a03f9f36e1f20a78
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

Loading…