Water → HCID 46836756, compound

HRID 474222Notes

Reaction equation

HRID 474222 reaction equation
Cl[CH2:2][CH:3]([OH:6])[CH2:4][OH:5].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:13][C:14]1[CH:15]=[N:16][C:17]([C:20]2[CH:21]=[C:22]([CH:37]=[CH:38][CH:39]=2)[CH2:23][N:24]2[C:29](=[O:30])[CH:28]=[CH:27][C:26]([C:31]3[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=3)=[N:25]2)=[N:18][CH:19]=1.O>CC(C)=O>[OH:6][CH:3]([CH2:4][OH:5])[CH2:2][O:13][C:14]1[CH:15]=[N:16][C:17]([C:20]2[CH:21]=[C:22]([CH:37]=[CH:38][CH:39]=2)[CH2:23][N:24]2[C:29](=[O:30])[CH:28]=[CH:27][C:26]([C:31]3[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=3)=[N:25]2)=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72903-Chloro-1,2-propanediolHCID 10796Cesium carbonateHCID 59438049HCID 59438049, compound

Product 1

HCID 46836756HCID 46836756, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

75 mg (0.68 mmol) of 3-chloro-1,2-propanediol and 322 mg (0.99 mmol) of caesium carbonate are added to 150 mg (0.41 mmol) of 2-[3-(5-hydroxy-pyrimidin-2-yl)benzyl]-6-(1-methyl-1H-pyrazol-4-yl)-2H-pyridazin-3-one, and the mixture is suspended in acetone. The reaction mixture is stirred at 80° C. for 5 days. Water is added to the reaction mixture, which is then extracted a number of times with ethyl acetate, dried over sodium sulfate and evaporated. The crude product is purified by means of column chromatography on silica gel.

Workup

  1. extractionis then extracted a number of times with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe crude product is purified by means of column chromatography on silica gel

Sources & evidence

ORD record
ord-a35ed521ebe442eea318ef75896b3236
Source dataset
uspto-grants-2014_01
Patent number
US08637518B2

Reaction notes

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