Potassium Carbonate → HCID 68056723, compound

HRID 2278432Notes

Reaction equation

HRID 2278432 reaction equation
Br[C:2]1[C:3]([O:16][CH3:17])=[N:4][C:5]([N:8]2[CH2:13][C@H:12]([CH3:14])[O:11][C@H:10]([CH3:15])[CH2:9]2)=[N:6][CH:7]=1.[CH3:18][C:19]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][C@H:10]1[O:11][C@@H:12]([CH3:14])[CH2:13][N:8]([C:5]2[N:4]=[C:3]([O:16][CH3:17])[C:2]([C:23]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:18])[CH:24]=3)=[CH:7][N:6]=2)[CH2:9]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 69088090HCID 69088090, compound

Product 1

HCID 68056723HCID 68056723, compoundYield 1.4%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of cis-4-(5-bromo-4-methoxypyrimidin-2-yl)-2,6-dimethylmorpholine (671 mg, 2.22 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (632 mg, 2.89 mmol) and potassium carbonate (798 mg, 5.77 mmol) in 1,4-dioxane (3 mL) and water (0.5 mL) stirred in air at 20° C. was added solid tetrakis(triphenylphosphine) palladium(0) (128 mg, 0.111 mmol). The reaction mixture was stirred under argon at 100° C. overnight. The reaction mixture was allowed to cool to room temperature, diluted with water and extracted with ethyl acetate (×3). The ethyl acetate layers were combined, dried over magnesium sulfate and evaporated under reduced pressure. The crude product was added to a silica gel column and was eluted with dichloromethane/methanol/triethylamine (20:1:0.5). Collected fractions were evaporated to give the title compound (120 mg, 0.031 mmol, 1.393% yield). LC/MS [M+H]+=318.

Workup

  1. stirringThe reaction mixture was stirred under argon at 100° C. overnight
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate (×3)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. additionThe crude product was added to a silica gel column
  7. washwas eluted with dichloromethane/methanol/triethylamine (20:1:0.5)
  8. customCollected fractions were evaporated

Sources & evidence

ORD record
ord-8a8d4a27557846e58732b83bd1de846e
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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