Potassium Carbonate → HCID 90417904, compound

HRID 709989Notes

Reaction equation

HRID 709989 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[C:16]([O:24][CH3:25])=[N:17][C:18]([NH:21][CH2:22][CH3:23])=[N:19][CH:20]=3)=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1.C([O-])([O-])=O.[K+].[K+]>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.O1CCOCC1.O>[CH2:22]([NH:21][C:18]1[N:17]=[C:16]([O:24][CH3:25])[C:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:30]4[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=4)[CH:7]=3)=[CH:14][N:13]=2)=[CH:20][N:19]=1)[CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 90418657HCID 90418657, compound

Product 1

HCID 90417904HCID 90417904, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-(5-((2-chloropyridin-4-yl)oxy)pyridin-2-yl)-N-ethyl-4-methoxypyrimidin-2-amine (0.090 g, 0.25 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.060 g, 0.28 mmol), and K2CO3 (0.10 g, 0.76 mmol) in 5:1 dioxane/water (6 mL) was sparged with Ar, treated with Pd(PPh3)4 (0.03 g, 0.025 mmol), sparged again with Ar and heated at 90° C. for 7 h. The mixture was cooled to RT, quenched with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to obtain N-ethyl-4-methoxy-5-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (80 mg, 79%). MS (ESI) m/z: 404.2 (M+H+).

Workup

  1. customwas sparged with Ar
  2. customsparged again with Ar
  3. temperatureThe mixture was cooled to RT
  4. customquenched with satd
  5. extractionNaHCO3, extracted with EtOAc (3×)
  6. washthe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-008de954a1184cc6841dff669b3eb14f
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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