Sodium Cyanide → 4-Propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile

HRID 733168Notes

Reaction equation

HRID 733168 reaction equation
[C-:1]#[N:2].[Na+].CS([C:8]1[N:13]=[C:12]([CH2:14][CH2:15][CH3:16])[CH:11]=[C:10]([Sn:17]([CH3:20])([CH3:19])[CH3:18])[N:9]=1)(=O)=O>CS(C)=O>[CH2:14]([C:12]1[CH:11]=[C:10]([Sn:17]([CH3:20])([CH3:19])[CH3:18])[N:9]=[C:8]([C:1]#[N:2])[N:13]=1)[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 690477692-Methanesulfonyl-4-propyl-6-trimethylstannanyl-pyrimidine

Product 1

HCID 690493004-Propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium cyanide (0.63 g, 12.9 mmol) was added at room temperature to 2-methanesulfonyl-4-propyl-6-trimethylstannanyl-pyrimidine (2.34 g, 6.5 mmol) in DMSO (23 mL). The mixture was stirred at room temperature for 2 hours, then partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: Cyclohexane/Ethyl acetate 9/1) to give 4-propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile (1.53 g, 76%) as an off white solid (mp=62° C.).

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed over silica gel (eluent: Cyclohexane/Ethyl acetate 9/1)

Sources & evidence

ORD record
ord-a36362a38c144772a995a30cf38715bd
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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