Water → 2-[3-(5-bromopyrimidin-2-yl)benzyl]-6-phenoxy-2H-pyridazin-3-one

HRID 532418Notes

Reaction equation

HRID 532418 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]Cl)[CH:9]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[O:22]([C:29]1[CH:30]=[CH:31][C:32](=[O:35])[NH:33][N:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[CH2:14][N:33]2[C:32](=[O:35])[CH:31]=[CH:30][C:29]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:34]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 468893056-phenoxypyridazin-3(2H)-oneHCID 594380475-Bromo-2-(3-(chloromethyl)phenyl)pyrimidine

Product 1

HCID 584970712-[3-(5-bromopyrimidin-2-yl)benzyl]-6-phenoxy-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.3 2.59 g (9.14 mmol) of 5-bromo-2-(3-chloromethylphenyl)pyrimidine and 2.84 g (8.70 mmol) of caesium carbonate are added to a suspension of 1.64 g (8.70 mmol) of 6-phenoxy-2H-pyridazin-3-one in 17.5 ml of DMF, and the mixture is stirred at room temperature for 18 hours. Water is added to the reaction mixture. The precipitate formed is filtered off with suction, washed with water and dried in vacuo, giving 2-[3-(5-bromopyrimidin-2-yl)benzyl]-6-phenoxy-2H-pyridazin-3-one as colourless crystals; ESI 435, 437.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off with suction
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f15b5bad386c4d36901c05cc26fe441d
Source dataset
uspto-grants-2014_10
Patent number
US08853211B2

Reaction notes

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