Water → 4-[2-(4-Bromo-pyrazol-1-yl)-pyrimidin-4-yl]-morpholine

HRID 1784370Notes

Reaction equation

HRID 1784370 reaction equation
[Br:1][C:2]1[CH:3]=[N: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)[CH:13]=[CH:12][N:11]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([C:10]2[N:15]=[C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH:13]=[CH:12][N:11]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 163754-BromopyrazoleHCID 24758Sodium hydrideHCID 17146974-(2-Chloropyrimidin-4-yl)morpholine

Product 1

HCID 575925214-[2-(4-Bromo-pyrazol-1-yl)-pyrimidin-4-yl]-morpholineYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a cooled (0° C.) solution of 4-bromo-1H-pyrazole (0.74 g, 5.0 mmol) in anhydrous DMF (7 ml) was added NaH (60% dispersion in mineral oil, 0.22 g, 5.5 mmol) in a portionwise fashion over 10 minutes. The mixture was stirred like this for 30 minutes before the addition of 4-(2-chloro-pyrimidin-4-yl)-morpholine (21)(1.0 g, 5.00 mmol). The reaction was then heated under the influence of microwave radiation (120° C., 14 minutes, fixed hold time, high absorption setting). The reaction was then cooled to room temperature and water added (14 ml) which caused a precipitate to form. The solid was collected by filtration, washed with water and dried in a desiccator to give the title compound (1.44 g, 93%) in sufficiently pure form to be used without any further purification. m/z (LC-MS, ESP): 310 [M+H]+, R/T=3.08 mins.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customto form
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried in a desiccator

Sources & evidence

ORD record
ord-e4859d64ceb545569fb5aa9671242aef
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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