Sodium hydride → HCID 86716194, compound

HRID 512167Notes

Reaction equation

HRID 512167 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][C:8]#[N:9])[CH:4]=[N:3][CH:2]=1.Br[CH2:11][CH:12]1[CH2:14][CH2:13]1.[H-].[Na+]>CN(C=O)C>[CH:12]1([CH2:11][CH:7]([C:5]2[CH:6]=[N:1][CH:2]=[N:3][CH:4]=2)[C:8]#[N:9])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 20080445HCID 20080445, compound

Product 1

HCID 86716194HCID 86716194, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 2-(pyrimidin-5-yl)acetonitrile (1.8 g, 15.1 mmol) in DMF (20 mL) was degassed and (bromomethyl)cyclopropane was added (2.04 g, 15.1 mmol). The reaction mixture was cooled to −10° C., NaH was added (720 mg, 18.1 mmol, 60% in mineral oil) in portions under N2 and stirred at the same temperature for 45 mins. The reaction mixture was quenched with sat. NH4Cl and extracted with EtOAc (30 ml×3). The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purification by column chromatography on silica gel (petroleum ether: EtOAc=3:1) to give 3-cyclopropyl-2-(pyrimidin-5-yl)propanenitrile (2.25 g, yield: 85%).1H NMR (CDCl3 400 MHz): δ9.22 (s, 1H), 68.78 (s, 2H), 3.80 (t, J=8 Hz, 2H), 1.98-1.92 (m, 1H), 1.83-1.79 (m, 1H), 0.87-0.83 (m, 1H), 0.61-0.59 (m, 2H), 0.21-0.13 (m, 2H).

Workup

  1. customThe reaction mixture was quenched with sat. NH4Cl
  2. extractionextracted with EtOAc (30 ml×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurification by column chromatography on silica gel (petroleum ether: EtOAc=3:1)

Sources & evidence

ORD record
ord-ad2343b6369e49c1b1eb4904b3ed1596
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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