Sodium hydride → HCID 59184717, compound

HRID 426135Notes

Reaction equation

HRID 426135 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([O:10][CH3:11])[N:5]=[C:4]([O:12][CH3:13])[N:3]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][C:23]#[N:24])[CH:18]=[C:19]([Cl:21])[CH:20]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([CH:22]([C:2]2[C:7]([CH2:8][CH3:9])=[C:6]([O:10][CH3:11])[N:5]=[C:4]([O:12][CH3:13])[N:3]=2)[C:23]#[N:24])[CH:18]=[C:19]([Cl:21])[CH:20]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 126899782-(3,5-Dichlorophenyl)acetonitrileHCID 14135533HCID 14135533, compound

Product 1

HCID 59184717HCID 59184717, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-Chloro-5-ethyl-2,6-dimethoxy-pyrimidine (1.42 g, 7 mmol) and (3,5-Dichloro-phenyl)-acetonitrile (1.3 g, 7 mmol) in anhydrous DMF (14 ml) at 0° C. (ice bath) under nitrogen atmosphere, was portionwise added 60% sodium hydride (616 mg, 15.44 mmol). After stirring for 1 hr., the mixture was further stirred at room temperature for 18 hr. The mixture was then neutralized with aqueous saturated ammonium chloride solution and the crude product was extracted with ethyl acetate and purified by silica gel column chromatography (eluent, EA:hexanes (1:10)) to afford 2.1 g (85%) of the title compound as a white solid. m.p. 121-122° C.; 1H NMR (200 MHz, CDCl3) δ 1.03 (3H, t, J=7.4 Hz), 2.03-2.57 (2H, m), 3.98 (6H, s), 5.23 (1H, s), 7.33 (3H, s).

Workup

  1. stirring, the mixture was further stirred at room temperature for 18 hr
  2. extractionthe crude product was extracted with ethyl acetate
  3. custompurified by silica gel column chromatography (eluent, EA:hexanes (1:10))

Sources & evidence

ORD record
ord-1bc9920bc96848e48480d3aad118821b
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…