2-(Dimethylamino)ethanol → HCID 59589521, compound

HRID 1472815Notes

Reaction equation

HRID 1472815 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[Br:9][C:10]1[CH:11]=[N:12][C:13](Cl)=[N:14][CH:15]=1>O1CCCC1.[Cl-].[NH4+]>[Br:9][C:10]1[CH:11]=[N:12][C:13]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 59589521HCID 59589521, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

2-Dimethylaminoethanol (0.113 mL, 1.113 mmol) was suspended in anhydrous tetrahydrofuran (10 mL). Sodium hydride (60% in mineral oil, 0.134 g, 3.334 mmol) was added and the mixture was stirred for 5 minutes. 5-Bromo-2-chloropyrimidine (0.2 g, 1.03 mmol) was added and the mixture was stirred for 2 hours. The reaction mixture was diluted with 10% aqueous ammonium chloride and extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. LCMS method: 1, RT: 0.63 min, MI: 246-248 [M+1].

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ffb529897d24b16b2d93209b99387cc
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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