4-Bromopyrazole → HCID 1227312, compound

HRID 1784368Notes

Reaction equation

HRID 1784368 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)[N:13]=[C:12]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:11]=1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[N: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 163754-BromopyrazoleHCID 24758Sodium hydrideHCID 2249672-Chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazine

Product 1

HCID 1227312HCID 1227312, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 4-bromopyrazole (0.29 g, 2.0 mmol) in anhydrous DMF (4 ml) was added NaH (60% dispersion in mineral oil, 0.088 g, 2.2 mmol) in a portionwise fashion over 10 minutes. The mixture allowed to warm to room temperature where it was stirred for 30 minutes before the adition of 2-Chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (3b)(0.571 g, 2.00 mmol). The mixture was then heated under the influence of microwave radiation (120° C., 14 minutes). Upon cooling the reaction was diluted with water (10 ml) and filtered. The filtercake was washed with more cold water (10 ml), collected and dried to give the title compound (92.4%, 0.73 g) in suitably pure form to be used without any further purification. m/z (LC-MS, ESP): 396 [M+H]+, R/T=3.56 mins.

Workup

  1. temperatureThe mixture was then heated under the influence of microwave radiation (120° C., 14 minutes)
  2. temperatureUpon cooling the reaction
  3. filtrationfiltered
  4. washThe filtercake was washed with more cold water (10 ml)
  5. customcollected
  6. customdried

Sources & evidence

ORD record
ord-615c3aa143234bda9e401a7d4278a91e
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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