2-(Dimethylamino)ethanol → HCID 59589521, compound

HRID 1593421Notes

Reaction equation

HRID 1593421 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](S(C)(=O)=O)=[N:14][CH:15]=1>CN(C)C=O>[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

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 3192865-Bromo-2-(methylsulphonyl)pyrimidine

Product 1

HCID 59589521HCID 59589521, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N,N-dimethylethanolamine (0.23 ml, 2.3 mmol) in dry dimethylformamide (5 ml) was treated with sodium hydride (60% suspension in mineral oil, 0.092 g, 2.3 mmol) and heated at 50° C. for 30 minutes. The product from Step 2 (0.50 g, 2.1 mmol) was added and the reaction heated at 50° C. overnight. After cooling to room temperature the reaction mixture was applied to a SCX column and washed with methanol then a mixture of 0.880 ammonia/methanol (1:9). The basic fractions were combined and chromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane solution (0.1:1.9:98 and 0.5:4.5:95) to afford the title compound (0.25 g, 48%); 1H NMR (CDCl3) 8.52 (2H, s), 4.45 (2H, t, J 8 Hz), 2.74 (2H, t, J 8 Hz), 2.33 (6H, s).

Workup

  1. temperaturethe reaction heated at 50° C. overnight
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. washwashed with methanol
  4. additiona mixture of 0.880 ammonia/methanol (1:9)
  5. customchromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane solution (0.1:1.9:98 and 0.5:4.5:95)

Sources & evidence

ORD record
ord-fe66db5fec22424ca3a88a217269aad5
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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