Sodium Cyanide → 4-Cyclopropylpyrimidine-2-carbonitrile

HRID 931126Notes

Reaction equation

HRID 931126 reaction equation
[N:1]1(C2CCCCCCC2)[CH2:8]CCCCCN1.Cl[C:18]1[N:23]=[C:22]([CH:24]2[CH2:26][CH2:25]2)[CH:21]=[CH:20][N:19]=1.[C-]#N.[Na+]>CS(C)=O.O>[CH:24]1([C:22]2[CH:21]=[CH:20][N:19]=[C:18]([C:8]#[N:1])[N:23]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 249019152-Chloro-4-cyclopropylpyrimidineHCID 66583054Diazabicyclooctane

Product 1

HCID 670586444-Cyclopropylpyrimidine-2-carbonitrileYield 803.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of diazabicyclooctane (0.013 g, 0.12 mmol) in dimethylsulfoxide and water was added a solution of 2-chloro-4-cyclopropylpyrimidine (0.2 g, 1.2 mmol) in dimethylsulfoxide followed by sodium cyanide (0.066 g, 1.3 mmol). The reaction mixture was stirred at room temperature for 48 h. The mixture was then poured into water and extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. The crude compound was purified via flash chromatography (10% ethyl acetate in petroleum ether) to afford 4-cyclopropylpyrimidine-2-carbonitrile (0.14 g, 77%). MS (ES+APCI) (M+H) 146.1; LCMS retention time 3.054 min (Method J).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified via flash chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-aa4d59161afb4eefb0a4c12c62d8f791
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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