Sodium hydride → [6-(Butyl-ethyl-amino)-2,5-dimethylpyrimidin-4-yl]-(2,4,6-trimethylphenyl)-acetonitrile

HRID 1831631Notes

Reaction equation

HRID 1831631 reaction equation
[C:1]1([CH3:12])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10]#[N:11].[H-].[Na+].[CH2:15]([N:19]([C:22]1[C:27]([CH3:28])=[C:26](Cl)[N:25]=[C:24]([CH3:30])[N:23]=1)[CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18]>CS(C)=O>[CH2:15]([N:19]([CH2:20][CH3:21])[C:22]1[N:23]=[C:24]([CH3:30])[N:25]=[C:26]([CH:9]([C:2]2[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=2[CH3:12])[C:10]#[N:11])[C:27]=1[CH3:28])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 21912306Butyl-(6-chloro-2,5-dimethylpyrimidin-4-yl)-ethylamine

Product 1

HCID 21912391[6-(Butyl-ethyl-amino)-2,5-dimethylpyrimidin-4-yl]-(2,4,6-trimethylphenyl)-acetonitrileYield 107.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of mesitylacetonitrile (66 mg, 0.41 mmol) in 1 ml of DMSO was treated with NaH (60% in oil, 20 mg, 0.50 mmol) and stirred at room temperature for 20 minutes, butyl-(6-chloro-2,5-dimethylpyrimidin-4-yl)-ethylamine (100 mg, 0.414 mmol) was added and the resulting mixture was heated at 130° C. for 15 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 160 mg of brown oil. The oil was purified through silica gel column chromatography using 5% ethyl acetate in hexane as eluent to give the title compound as a brown oil. 1H NMR (CDCl3) δ 6.83 (s, 2H), 5.49 (s, 1H), 3.2–3.4 (m, 2H), 3.0–3.2 (m, 2H), 2.51 (s, 3H), 2.24 (s, 3H), 2.21 (s, 6H), 1.66 (s, 3H), 1.35–1.50 (m, 2H), 1.1–1.3 (m, 2H), 1.05 (t, 3H), 0.84 (t, 3H) ppm.

Workup

  1. temperaturethe resulting mixture was heated at 130° C. for 15 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-538b66755f364622950728b686b45aa4
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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