Sodium Carbonate → HCID 178509578, compound

HRID 2367354Notes

Reaction equation

HRID 2367354 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][CH:22]=[CH:21][CH:20]=4)[N:18]=3)[CH2:9]2)[N:5]=[C:4]([NH2:25])[N:3]=1.[F:26][C:27]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30].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>[NH2:25][C:4]1[N:3]=[C:2]([C:33]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([F:26])[CH:34]=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][CH:22]=[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 178508444HCID 178508444, compound

Product 1

HCID 178509578HCID 178509578, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
140 °C

Procedure

A mixture of crude 4-chloro-6-[2-(4-phenyl-1H-imidazol-2-yl)-4-morpholinyl]-2-pyrimidinamine, 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (765 mg, 3.10 mmol), Na2CO3 (631 mg, 5.96 mmol) and Pd(PPh3)4 (275 mg, 0.238 mmol) in 1,4-dioxane (6 mL) and water (2 mL) was heated at 140° C. under microwave conditions with stirring for 1.0 hour. The mixture was filtered, washed by EtOAc (150 mL), and concentrated to afford the crude title compound (1.3 g) as a yellow solid. This material was combined with another batch of crude title compound (100 mg). The combined material was washed by EtOAc (150 mL), and concentrated. The resulting residue was purified by silica gel chromatography using EtOAc in petroleum ether from 50% to 70% to afford the title compound (400 mg) as a light yellow solid. LC-MS (ES) m/z=442 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed by EtOAc (150 mL)
  3. concentrationconcentrated
  4. customto afford the crude title compound (1.3 g) as a yellow solid
  5. washThe combined material was washed by EtOAc (150 mL)
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2b2d5b8decb470fb1052419168f9c8b
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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