Potassium Carbonate → HCID 58966971, compound

HRID 252639Notes

Reaction equation

HRID 252639 reaction equation
OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[CH3:15][NH:16][C:17]1[N:22]=[C:21]([C:23]2[C:24]([O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:37]([NH2:39])=[NH:38])=[CH:32][CH:31]=3)=[N:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:47]([CH3:56])[C:48]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=O.CO.O>CS(C)=O>[CH3:15][NH:16][C:17]1[N:22]=[C:21]([C:23]2[C:24]([O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:37]4[NH:39][C:47]([CH3:56])=[C:48]([C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)[N:38]=4)=[CH:32][CH:31]=3)=[N:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 164522-BromopropiophenoneHCID 22242641Methanol--water (1/1)HCID 178482366HCID 178482366, compound

Product 1

HCID 58966971HCID 58966971, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 1-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)guanidine bis-TFA salt (0.200 g, 0.35 mmol) and potassium carbonate (0.20 g, 1.4 mmol) in 1 mL DMSO was added 2-bromo-1-phenylpropan-1-one (0.054 ml, 0.35 mmol). The reaction was allowed to stir at ambient temperature for 30 min, then 70° C. After 16 h, the reaction was quenched by addition of water and was extracted with EtOAc. The organic layer was dried over anhyd. Sodium sulfate, filtered, and concentrated in vacuo. The resulting green/brown oil was purified by silica gel chromatography (40 g, 0-100% 90/10 MC/MeOH in MC) to give an oil. This was lyophilized from MeOH/water to give N-methyl-4-(2-(4-(5-methyl-4-phenyl-1H-imidazol-2-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-amine as an off-white solid. MS m/z=450 [M+H]+. Calc'd for C26H23N7O: 449.5.

Workup

  1. custom70° C
  2. waitAfter 16 h
  3. customthe reaction was quenched by addition of water
  4. extractionwas extracted with EtOAc
  5. customThe organic layer was dried over anhyd
  6. filtrationSodium sulfate, filtered
  7. concentrationconcentrated in vacuo
  8. customThe resulting green/brown oil was purified by silica gel chromatography (40 g, 0-100% 90/10 MC/MeOH in MC)
  9. customto give an oil

Sources & evidence

ORD record
ord-50cc374cf2bd45d7bb692ab43ce02fe4
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Reaction notes

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