Sodium Iodide → HCID 178461603, compound

HRID 1775497Notes

Reaction equation

HRID 1775497 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[N:6]=[C:5]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]2[CH3:17])[N:4]=1.[I-].[Na+].[Si](Cl)(C)(C)C.S(=O)(=O)(O)[O-].[Na+]>C(#N)C.O>[CH3:17][C@H:12]1[CH2:13][O:14][CH2:15][CH2:16][N:11]1[C:5]1[N:4]=[C:3]([OH:2])[CH:8]=[C:7]([OH:9])[N:6]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516919Sodium BisulfateHCID 118436035HCID 118436035, compound

Product 1

HCID 178461603HCID 178461603, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(3S)-4-(4,6-Dimethoxypyrimidin-2-yl)-3-methylmorpholine (6.3 g, 26.3 mmol) was dissolved in acetonitrile (88 mL). Argon was bubbled into the solution and sodium iodide (11.8 g, 79.0 mmol) and TMS-Cl (10.3 mL, 79.0 mmol) were added. The reaction was heated under reflux for 2 h, and then allowed to cool to room temperature. Water (50 mL) and sodium bisulfate (2.74 g, 26.3 mmol) was added. Acetonitrile was removed by rotary evaporation and the resulting slurry was filtered. The precipitate was suspended in ethanol and concentrated to dryness by rotary evaporation to give the title compound (3.81 g, 68%). 1H NMR (400 MHz, DMSO-d6) δ 10.61 (br s, 2 H), 4.80 (br s, 1 H), 4.40 (d, J=5.9 Hz, 1 H), 3.98 (d, J=12.7 Hz, 1 H), 3.85 (dd, J=11.3, 3.5 Hz, 1 H), 3.68-3.62 (m, 1 H), 3.56-3.50 (m, 1 H), 3.38 (td, J=11.8, 3.0 Hz, 1 H), 3.16-3.04 (m, 1 H), 1.16 (d, J=6.7 Hz, 3 H).

Workup

  1. additionwere added
  2. temperatureThe reaction was heated
  3. temperatureunder reflux for 2 h
  4. customAcetonitrile was removed by rotary evaporation
  5. filtrationthe resulting slurry was filtered
  6. concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-10c5edad436742c5b45c7ac5e33a21ce
Source dataset
uspto-grants-2016_02
Patent number
US09260439B2

Reaction notes

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