Potassium Carbonate → N-methyl-4-(2-(4-(4-phenylphthalazin-1-yloxy)phenoxy)pyridin-3-yl)pyrimidin-2-amine

HRID 593981Notes

Reaction equation

HRID 593981 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:3]=1.[CH3:18][NH:19][C:20]1[N:25]=[C:24]([C:26]2[C:27]([O:32][C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CO>[CH3:18][NH:19][C:20]1[N:25]=[C:24]([C:26]2[C:27]([O:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:4][N:3]=4)=[CH:37][CH:38]=3)=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2721091-Chloro-4-phenylphthalazineHCID 66732110HCID 66732110, compound

Product 1

HCID 57756246N-methyl-4-(2-(4-(4-phenylphthalazin-1-yloxy)phenoxy)pyridin-3-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A mixture of 1-chloro-4-phenylphthalazine (0.0900 g, 0.374 mmol), 4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenol (0.110 g, 0.374 mmol), and potassium carbonate (0.129 g, 0.934 mmol) in 1 mL DMSO was heated in a sealed tube for 1 h. Upon cooling, a white precipitate formed. The material was partitioned between water and DCM. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give a crude solid, which was suspended in MeOH, sonicated, filtered and dried to give N-methyl-4-(2-(4-(4-phenylphthalazin-1-yloxy)phenoxy)pyridin-3-yl)pyrimidin-2-amine as a white solid. MS m/z=499 [M+H]+. Calc'd for C30H22N6O2: 498.5.

Workup

  1. temperaturewas heated in a sealed tube for 1 h
  2. temperatureUpon cooling
  3. customa white precipitate formed
  4. customThe material was partitioned between water and DCM
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude solid, which
  9. customsonicated
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-7a83ad1b93e84ae4be487ea88d3f0cd4
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

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