Potassium Carbonate → HCID 90416753, compound

HRID 709982Notes

Reaction equation

HRID 709982 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:16]3[C:17]([O:25][CH3:26])=[N:18][C:19]([NH:22][CH2:23][CH3:24])=[N:20][CH:21]=3)=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.[CH3:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH2:23]([NH:22][C:19]1[N:18]=[C:17]([O:25][CH3:26])[C:16]([C:12]2[CH:11]=[CH:10][C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:31]4[CH:30]=[N:29][C:28]([CH3:27])=[CH:33][CH:32]=4)[CH:7]=3)=[C:14]([CH3:15])[N:13]=2)=[CH:21][N:20]=1)[CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 164142722-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 90416638HCID 90416638, compound

Product 1

HCID 90416753HCID 90416753, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example C1 (0.15 g, 0.4 mmol) and 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.13 g, 0.57 mmol) in dioxane (4 mL) was sparged with Ar, treated with a solution of K2CO3 (0.11 g, 0.8 mmol) in water (1 mL) and heated at 90° C. for 2 h. The mixture was cooled to RT, diluted with water, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (MeOH/DCM) to afford N-ethyl-4-methoxy-5-(6-methyl-5-((6′-methyl-[2,3′-bipyridin]-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine as an orange foam (0.106 g, 61%). 1H NMR (400 MHz, DMSO-d6): δ 9.11 (d, J=2.4 Hz, 1H), 8.74 (s, 1H), 8.54 (d, J=5.7 Hz, 1H), 8.29 (dd, J=8.1, 2.4 Hz, 1H), 7.77 (d, J=8.6 Hz, 1H), 7.65 (d, J=2.4 Hz, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.34 (d, J=8.2 Hz, 1H), 7.02 (d, J=1.9 Hz, 1H), 6.79 (dd, J=5.7, 2.4 Hz, 1H), 3.96 (s, 3H), 3.36-3.34 (m, 2H), 2.51 (s, 3H), 2.38 (s, 3H), 1.15 (s, 3H); MS (ESI) m/z: 429.2 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc (3×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-423eb2242f3e4f20ac8ae894d37f0495
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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