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

HRID 2361072Notes

Reaction equation

HRID 2361072 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-c9f49cf16ced49869a630a52bc60ae15
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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