Sodium hydride → HCID 89581270, compound

HRID 1501149Notes

Reaction equation

HRID 1501149 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:12])[CH3:11])=[CH:6][CH:5]=1.Cl[C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:12][C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH3:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 953521-(4-Bromophenyl)ethanol

Product 1

HCID 89581270HCID 89581270, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

NaH (300 mg, 60%, 7.5 mmol) was suspended in N,N-dimethylformamide. 1-(4-bromophenyl)ethanol was added to the above mixture and stirred at 40° C. for 0.5 hour. Then 2-chloropyrimidine was added to the above mixture and stirred at 100° C. for 12 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=3:1) to give 2-(1-(4-bromophenyl)ethoxy)pyrimidine as a white solid (2.6 g, 94%). LRMS (M+H+) m/z: calcd 278.01. found 278.

Workup

  1. stirringstirred at 100° C. for 12 hours
  2. concentrationThe mixture was concentrated
  3. customto give a residue
  4. customThe residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3d04a0fa34bf4256a176ada2470fb7c0
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…