Cesium carbonate → N-(4-(5-iodopyrimidin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

HRID 227800Notes

Reaction equation

HRID 227800 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[C:8]1([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)=[N:16][N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:33]1[C:38]([I:39])=[CH:37][N:36]=[CH:35][N:34]=1>CS(C)=O.O>[I:39][C:38]1[C:33]([O:31][C:28]2[CH:27]=[CH:26][C:25]([NH:24][C:17]3[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:14]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)=[N:15][N:16]=3)=[CH:30][CH:29]=2)=[N:34][CH:35]=[N:36][CH:37]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 112302044-Chloro-5-iodopyrimidineHCID 1364007234-(4-Phenylphthalazin-1-ylamino)phenol hydrochloride

Product 1

HCID 66731498N-(4-(5-iodopyrimidin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a brown mixture of cesium carbonate (2.79 g, 8.58 mmol) and 4-(4-phenylphthalazin-1-ylamino)phenol hydrochloride (1.00 g, 2.86 mmol) in 10 mL DMSO was added 4-chloro-5-iodopyrimidine (0.687 g, 2.86 mmol). The reaction was allowed to stir at RT for 1 h. The reaction was heated to and maintained at 70° C. overnight. The reaction was cooled and diluted with water. The solid was filtered and dried in vacuo to give N-(4-(5-iodopyrimidin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine as a gray solid. MS m/z=518 [M+H]+. Calc'd for C24H16IN5O: 517.3.

Workup

  1. temperatureThe reaction was heated to and
  2. temperaturemaintained at 70° C. overnight
  3. temperatureThe reaction was cooled
  4. filtrationThe solid was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-43990bde66e54f97af59caa2ef7fa561
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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