Potassium Carbonate → 3-((3-(5-fluoro-2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)amino)-4-methyl-N-(3-(1-methylethyl)phenyl)benzamide

HRID 1361654Notes

Reaction equation

HRID 1361654 reaction equation
Cl[C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][N:11]=[C:10]([NH:15][CH3:16])[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=1)=[O:22].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:14][C:13]1[C:8]([C:7]2[C:2]([NH:17][C:18]3[CH:19]=[C:20]([CH:33]=[CH:34][C:35]=3[CH3:36])[C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=3)=[O:22])=[N:3][CH:4]=[CH:5][CH:6]=2)=[N:9][C:10]([NH:15][CH3:16])=[N:11][CH:12]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 251022283-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamideHCID 86602592[4-(2-Chloro-pyridin-3-yl)-5-fluoro-pyrimidin-2-yl]-methyl-amine

Product 1

HCID 585882223-((3-(5-fluoro-2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)amino)-4-methyl-N-(3-(1-methylethyl)phenyl)benzamide

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

[4-(2-Chloro-pyridin-3-yl)-5-fluoro-pyrimidin-2-yl]-methyl-amine (62 mg, 0.26 mmol), 3-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide (84 mg, 0.31 mmol), Pd(OAc)2 (6 mg, 0.03 mmol), rac-BINAP (16 mg, 0.03 mmol) and K2CO3 (719 mg, 5.2 mmol) in toluene (3.0 mL) were reacted overnight at 130° C. The reaction was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filter, concentrated and purified by reverse-phase HPLC (Gilson, acidic mobile phase) yielding the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfilter
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (Gilson, acidic mobile phase)

Sources & evidence

ORD record
ord-1e4c4f3e22534b44b16171ff7b1b484b
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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