Trimethylsilyl cyanide → 2-(3-Hydroxypropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile

HRID 512205Notes

Reaction equation

HRID 512205 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[N:11][CH:12]=1.C[Si]([C:18]#[N:19])(C)C>C(Cl)Cl.[I-].[Zn+2].[I-]>[OH:1][CH2:6][CH2:5][CH2:4][O:3][CH:2]([C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[N:11][CH:12]=1)[C:18]#[N:19]

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 867162345-(1,3-Dioxan-2-yl)-2-methylpyrimidine

Product 1

HCID 867162352-(3-Hydroxypropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 5-(1,3-dioxan-2-yl)-2-methylpyrimidine (140 mg, 0.78 mmol) in DCM (5.0 ml) was added zinc iodide (124 mg, 0.39 mmol). Trimethylsilyl cyanide (116 mg, 0.155 ml, 1.17 mmol) was added dropwise over a period of 10 minutes. Cooling was removed and the reaction was stirred for 40 hours at room temperature. The mixture was poured into H2O (20 mL) and extracted with DCM (3×20 mL), the combined org. phases were washed with brine, dried over MgSO4 and concetrated in vacuo. The crude product was used for next step without further purification.

Workup

  1. temperatureCooling
  2. customwas removed
  3. additionThe mixture was poured into H2O (20 mL)
  4. extractionextracted with DCM (3×20 mL)
  5. washphases were washed with brine
  6. dry with materialdried over MgSO4
  7. customThe crude product was used for next step without further purification

Sources & evidence

ORD record
ord-477fabcd63da4690bd2f007b21273973
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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