Cesium carbonate → HCID 53380742, compound

HRID 1771549Notes

Reaction equation

HRID 1771549 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:3]=1.[CH:14]1([NH:17][C:18](=[O:35])[NH:19][C:20]2[CH:25]=[CH:24][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:14]1([NH:17][C:18]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)[N:3]=3)=[CH:22][CH:21]=2)=[O:35])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 8246434-(4-Chloropyrimidin-2-yl)morpholineHCID 44119149N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

Product 1

HCID 53380742HCID 53380742, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(4-chloropyrimidin-2-yl)morpholine (80 mg, 0.40 mmol) and (4-(3-cyclopropylureido)phenyl)boronic acid pinacol ester (145 mg, 0.48 mmol) in dioxane (2 mL) was added Pd(PPh3)2Cl2 (14 mg, 0.02 mmol) and Cs2CO3 (2M aq solution, 0.3 mL). The reaction mixture was then heated to reflux for 16 h. The crude reaction mixture was then partitioned between water and EtOAc, the phases separated and the organic layer washed with aqueous NaHCO3 and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (0-5% EtOAc/MeOH) to yield a white solid (7.8 mg, 6%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 16 h
  3. customThe crude reaction mixture
  4. customwas then partitioned between water and EtOAc
  5. customthe phases separated
  6. washthe organic layer washed with aqueous NaHCO3 and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customThe residue was purified by flash chromatography (0-5% EtOAc/MeOH)

Sources & evidence

ORD record
ord-696307e215554ca484a981da7f3b5f94
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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