Dichloromethane → 2-Isopropoxy-2-(2-methylpyrimidin-5-yl)acetonitrile

HRID 512200Notes

Reaction equation

HRID 512200 reaction equation
C(O[CH:5]([O:13][CH:14]([CH3:16])[CH3:15])[C:6]1[CH:7]=[N:8][C:9]([CH3:12])=[N:10][CH:11]=1)(C)C.C(Cl)Cl.[Si]([C:24]#[N:25])(C)(C)C>[I-].[I-].[Zn+2].O>[CH:14]([O:13][CH:5]([C:6]1[CH:11]=[N:10][C:9]([CH3:12])=[N:8][CH:7]=1)[C:24]#[N:25])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 82115Trimethylsilyl cyanideHCID 867162275-(Diisopropoxymethyl)-2-methylpyrimidine

Product 1

HCID 867162292-Isopropoxy-2-(2-methylpyrimidin-5-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalyst2×HCID 962WaterSolvent

Procedure

A solution of 5-diisopropoxymethyl-2-methyl-pyrimidine (335 mg, 1.49 mmol) in DCM (5 mL, 80 mmol) was cooled at 0° C. Zinc diiodide (47.7 mg, 0.149 mmol) TMSCN (219 uL, 1.64 mmol) were added and cooling removed. After stirring for 24 hours TLC indicated that starting materiale was present. TMSCN (60 uL, 0.45 mmol) and zinc diiodide (48 mg, 0.15 mmol) were added and the reaction was stirred for a further 3.5 hours. The reaction was poured into water (20 mL) and extracted with DCM (3×20 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography 2-Isopropoxy-2-(2-methylpyrimidin-5-yl)acetonitrile (217 mg, 76%).

Workup

  1. temperaturecooling
  2. customremoved
  3. stirringthe reaction was stirred for a further 3.5 hours
  4. extractionextracted with DCM (3×20 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography 2-Isopropoxy-2-(2-methylpyrimidin-5-yl)acetonitrile (217 mg, 76%)

Sources & evidence

ORD record
ord-0b1919378f094bafafe272044fc29e41
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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