2-Bromoethyl methyl ether → HCID 86716220, compound

HRID 512191Notes

Reaction equation

HRID 512191 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][N:4]=1.Br[CH2:15][CH2:16][O:17][CH3:18].CC([O-])(C)C.[K+]>O1CCOCC1>[CH3:18][O:17][CH2:16][CH2:15][CH:9]([C:6]1[CH:7]=[N:8][C:3]([C:2]([F:1])([F:12])[F:13])=[N:4][CH:5]=1)[C:10]#[N:11]

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 23665647Potassium tert-butoxideHCID 84770235HCID 84770235, compound

Product 1

HCID 86716220HCID 86716220, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(2-(trifluoromethyl)pyrimidin-5-yl)acetonitrile (500 mg, 2.67 mmol) and 1-bromo-2-methoxyethane (419 mg, 2.81 mmol) in 1,4-dioxane (5 mL) was degassed and added t-BuOK (2.81 mL, 2.81 mmol, 1M in THF) at 0° C. The resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched by sat.NH4Cl and extracted with EtOAc (3×10 mL). The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography (EtOAc: petroleum ether=1:10) to give 4-methoxy-2-(2-(trifluoromethyl)pyrimidin-5-yl)butanenitrile (100 mg, yield: 15%, 85% purity in LCMS, [M+H]=246).

Workup

  1. customThe reaction mixture was quenched
  2. extractionNH4Cl and extracted with EtOAc (3×10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column chromatography (EtOAc: petroleum ether=1:10)

Sources & evidence

ORD record
ord-29054d401915485dbc4aafec80622755
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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