Sodium Carbonate → HCID 178488779, compound

HRID 2367369Notes

Reaction equation

HRID 2367369 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[NH:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[N:18]=3)[CH2:9]2)[N:5]=[C:4]([NH2:27])[N:3]=1.[F:28][C:29]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[CH:33][C:30]=1[C:31]#[N:32].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:27][C:4]1[N:3]=[C:2]([C:35]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([F:28])[CH:36]=2)[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[NH:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[N:18]=3)[CH2:9]2)[N:5]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 513509512-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 178488780HCID 178488780, compound

Product 1

HCID 178488779HCID 178488779, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-chloro-6-(2-{4-[4-(methyloxy)phenyl]-1H-imidazol-2-yl}-4-morpholinyl)-2-pyrimidinamine (1.0 g, 2.59 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (0.83 g, 3.36 mmol), Na2CO3 (0.685 g, 6.46 mmol) and Pd(PPh3)4 (0.30 g, 0.26 mmol) in 1,4-dioxane (8 mL) and water (2 mL) was heated at 140° C. under microwave conditions with stirring for 1 hour. The reaction mixture was filtered, washed by ethyl acetate (100 mL), and concentrated. The resulting residue was purified by silica gel chromatography using EtOAc/petroleum ether (3:1) to afford the title compound (675 mg) as a yellow solid. LC-MS (ES) m/z=472 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed by ethyl acetate (100 mL)
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-343b1ac8652d4f3bbbf510bad71d79d6
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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