Sodium hydride → 2-[(6-Chloropyrimidin-4-yl)oxy]quinoxaline

HRID 1846449Notes

Reaction equation

HRID 1846449 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[N:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[Cl:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1>CN(C=O)C>[Cl:14][C:15]1[N:16]=[CH:17][N:18]=[C:19]([O:3][C:4]2[CH:13]=[N:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 178516710HCID 178516710, compound

Product 1

HCID 457890432-[(6-Chloropyrimidin-4-yl)oxy]quinoxaline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40 mg (0.92 mmol) sodium hydride (55%, suspension in mineral oil) were added to 0.10 g (0.68 mmol) 2-hydroxyquinoxaline in 1.5 mL DMF and the mixture was stirred for 15 min. Then 0.11 g (0.69 mmol) 4,6-dichloropyrimidine were added and the mixture was stirred overnight at RT. The reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined, the acetonitrile was eliminated i.vac., and the precipitated product was suction filtered and dried.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. customThe reaction mixture was purified by preparative HPLC-MS
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-aa4000d5274546968ce4fc0a34fa18d2
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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