Sodium hydride → HCID 68599736, compound

HRID 1784367Notes

Reaction equation

HRID 1784367 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[H-].[Na+].Cl[C:10]1[N:15]=[C:14]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:13]=[C:12]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:11]=1>CN(C)C=O.O>[Br:1][C:2]1[NH:3][CH2:4][N:5]([C:10]2[N:15]=[C:14]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[N:13]=[C:12]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[N:11]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2249672-Chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazineHCID 178418934HCID 178418934, compound

Product 1

HCID 68599736HCID 68599736, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a cooled solution of 4-bromo-1H-imidazole (0.249 g, 2.0 mmol) in anhydrous dimethylformamide (4 ml) was slowly added sodium hydride (60% dispersion in mineral oil) (0.088 g, 2.2 mmol). When the evolution of gas has ceased (30 mins), 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (3b)(0.571 g, 2.00 mmol) was added in a single portion and the resulting mixture heated in a microwave reactor at 120° C. for exactly 14 minutes (fixed temperature holdtime, high absorbtion setting). The resulting brown/yellow slurry was diluted with water (10 ml) and filtered. The filter cake was washed with cold water (2×10 ml) and then dried in a vacuum dessicator to give the title compound in suitably pure form to be used without further purification. m/z (LC-MS, ESP): 396 [M+H]+, R/T=3.61 mins.

Workup

  1. additionwas added in a single portion
  2. filtrationfiltered
  3. washThe filter cake was washed with cold water (2×10 ml)
  4. customdried in a vacuum dessicator

Sources & evidence

ORD record
ord-17fe669a02fd4025b1fe360eec5247ad
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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