Sodium Cyanide → HCID 49862367, compound

HRID 733167Notes

Reaction equation

HRID 733167 reaction equation
[C-:1]#[N:2].[Na+].[CH:4]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][CH3:21])[N:16]=[C:15](S(C)(=O)=O)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)([CH3:6])[CH3:5]>CS(C)=O>[CH:4]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][CH3:21])[N:16]=[C:15]([C:1]#[N:2])[N:14]=2)[CH:10]=[CH:11][CH:12]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 69048427HCID 69048427, compound

Product 1

HCID 49862367HCID 49862367, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium cyanide (65 mg, 1.32 mmol) was added at room temperature to 4-(3-isopropyl-phenyl)-2-methanesulfonyl-6-propyl-pyrimidine (211 mg) in DMSO (2 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 7/3) to afford a pink oil which crystallised in pentane. After filtration, 4-(3-isopropyl-phenyl)-2-cyano-6-propyl-pyrimidine (164 mg) was obtained as an off white solid (mp=64° 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 7/3)
  8. customto afford a pink oil which
  9. customcrystallised in pentane
  10. filtrationAfter filtration

Sources & evidence

ORD record
ord-751c1c61de244f20b493bef212de509f
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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