Sodium Carbonate → HCID 50905497, compound

HRID 1431252Notes

Reaction equation

HRID 1431252 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH3:18])=[C:16]([NH:19][C:20]2[CH:25]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:23]=[CH:22][C:21]=2[N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.Cl[C:42]1[CH:47]=[C:46]([CH3:48])[N:45]=[C:44]([NH2:49])[N:43]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:49][C:44]1[N:43]=[C:42]([C:24]2[CH:23]=[CH:22][C:21]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[C:20]([NH:19][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[C:17]=3[CH3:18])[CH:25]=2)[CH:47]=[C:46]([CH3:48])[N:45]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 312751,4-DioxaneHCID 59631147HCID 59631147, compound

Product 1

HCID 50905497HCID 50905497, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-(2-fluorophenyl)-3-methyl-N-(2-morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinolin-4-amine (100 mg, 0.185 mmol; described herein), 4-chloro-6-methylpyrimidin-2-amine (26.6 mg, 0.185 mmol), sodium carbonate (58.9 mg, 0.556 mmol), dichlorobis(triphenylphosphine)-palladium(ii) (13.0 mg, 0.019 mmol), 1,4-dioxane (4.0 mL), and water (1.0 mL) was heated in a microwave at 120° C. for 60 min. The mixture was then cooled to rt and partitioned between EtOAc and water. The organic layer was dried (magnesium sulfate) and concd, and chromatography afforded N-(5-(2-amino-6-methyl-4-pyrimidinyl)-2-(4-morpholinyl)phenyl)-2-(2-fluorophenyl)-3-methyl-4-quinolinamine. 1H NMR (400 MHz, TFA) δ ppm 8.32 (1H, dd, J=8.8, 2.2 Hz), 7.95-8.17 (5H, m), 7.72 (2H, m), 7.55 (1H, m), 7.40-7.48 (1H, m), 7.24-7.37 (2H, m), 4.30-4.47 (4H, m), 4.07-4.25 (4H, m), 2.60 (3H, s), 2.09 (3H, br. s.). Mass Spectrum (ESI) m/e=521.1 (M+1).

Workup

  1. temperatureThe mixture was then cooled to rt
  2. custompartitioned between EtOAc and water
  3. dry with materialThe organic layer was dried (magnesium sulfate) and concd, and chromatography

Sources & evidence

ORD record
ord-2b1d9372f42740779b510900fae4c5b7
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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