Sodium hydride → (3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

HRID 426132Notes

Reaction equation

HRID 426132 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH2:23][C:24]#[N:25])[CH:19]=[C:20]([Cl:22])[CH:21]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH:23]([C:2]2[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=2)[C:24]#[N:25])[CH:19]=[C:20]([Cl:22])[CH:21]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 126899782-(3,5-Dichlorophenyl)acetonitrileHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidine

Product 1

HCID 59184725(3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-Chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (9.8 g, 45 mmol) and (3,5-Dichloro-phenyl)-acetonitrile (8.0 g, 43 mmol) in anhydrous DMF (70 ml) at 0° C. (ice bath) under nitrogen atmosphere, was portionwise added 60% sodium hydride (3.44 g, 86 mmol). After stirring for 1 hr., the mixture was further stirred at room temperature for overnight. 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 (1:9)) to afford 9.6 g (61%) of the title compound as a white solid. m.p. 135-136° C.; 1H NMR (200 MHz, CDCl3) δ 1.13 (3H, d, J=7.0 Hz), 1.18 (3H, d, J=7.0 Hz), 2.97 (1H, m), 3.99 (6H, s), 5.33 (1H, s), 7.25-7.33 (3H, m).

Workup

  1. stirring, the mixture was further stirred at room temperature for overnight
  2. extractionthe crude product was extracted with ethyl acetate
  3. custompurified by silica gel column chromatography (eluent, EA:hexanes (1:9))

Sources & evidence

ORD record
ord-c8d0c89303dd4a0883ba1478c8d06eeb
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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