Potassium Carbonate → HCID 67116939, compound

HRID 1193196Notes

Reaction equation

HRID 1193196 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([N:11]1[CH2:18][CH2:17][C@@H:16]2[C@@H:13]([N:14]([C:19]3[N:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[N:20]=3)[CH2:15]2)[CH2:12]1)=[O:10].[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>O>[CH3:26][C:21]1[CH:22]=[C:23]([CH3:25])[N:24]=[C:19]([N:14]2[C@@H:13]3[C@@H:16]([CH2:17][CH2:18][N:11]([C:9]([C:3]4[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=4[C:31]4[CH:32]=[N:27][CH:28]=[N:29][CH:30]=4)=[O:10])[CH2:12]3)[CH2:15]2)[N:20]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 67116780HCID 67116780, compound

Product 1

HCID 67116939HCID 67116939, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Example 198 was prepared by the following procedure: (1R,6S)-3-[(2-bromo-5-fluorophenyl)carbonyl]-8-(4,6-dimethylpyrimidin-2-yl)-3,8-diazabicyclo[4.2.0]octane (100 mg, 0.24 mmol), pyrimidine-5-boronic acid (44 mg, 0.36 mmol), Pd(ddpf)Cl2 (19 mg, 0.02 mmol) and K2CO3 (98 mg, 0.72 mmol) were suspended a 1.2 ml of a mixture of 1,4-dioxane and water (5:1) in a sealed tube and heated to 150° C. for 2 h. The reaction was cooled to 23° C., and purified directly on 16 g SiO2 with 0-50% ethyl acetate/hexanes to give 24 mg (24% yield). MS (ESI) mass calcd. for C23H23FN6O, 418.5; m/z found, 419.2 [M+H]+.

Workup

  1. customExample 198 was prepared by the following procedure
  2. temperatureThe reaction was cooled to 23° C.
  3. custompurified directly on 16 g SiO2 with 0-50% ethyl acetate/hexanes
  4. customto give 24 mg (24% yield)

Sources & evidence

ORD record
ord-820136bc39e347758436ee06250f37ec
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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