Cesium carbonate → HCID 58539090, compound

HRID 2403475Notes

Reaction equation

HRID 2403475 reaction equation
Br[C:2]1[C:3]([NH:25][CH3:26])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])=[CH:11][C:10]=2[O:23][CH3:24])=[N:6][CH:7]=1.[CH:27]1([B-](F)(F)F)[CH2:30][CH2:29][CH2:28]1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].C12(P(C34CC5CC(CC(C5)C3)C4)CCCC)CC3CC(CC(C3)C1)C2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:27]1([C:2]2[C:3]([NH:25][CH3:26])=[N:4][C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])=[CH:11][C:10]=3[O:23][CH3:24])=[N:6][CH:7]=2)[CH2:30][CH2:29][CH2:28]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneHCID 25105160Potassium cyclobutyl(trifluoro)borate(1-)HCID 58539140HCID 58539140, compound

Product 1

HCID 58539090HCID 58539090, compoundYield 8.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
11 °C

Procedure

To a microwave tube was added (4-(5-bromo-4-(methylamino)pyrimidin-2-ylamino)-3-methoxyphenyl)(morpholino)methanone (100 mg, 0.24 mmol), potassium cyclobutyltrifluoroborate (177 mg, 1.1 mmol), cesium carbonate (0.23 g, 0.71 mmol), toluene (2.9 mL) and water (0.3 mL). The mixture was degassed by nitrogen bubbling for 15 minutes. di-(1-adamantyl)-n-butylphosphine (19 mg, 0.053 mmol) and palladium acetate (2.6 mg, 0.026 mmol) was then added. The reaction was sealed and heated at 11° C. for 2 hours. The reaction mixture was filtered and concentrated. The crude product was purified by RP-HPLC to give the desire product (8.1 mg, 8.6%).

Workup

  1. customThe mixture was degassed by nitrogen bubbling for 15 minutes
  2. customThe reaction was sealed
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-92fa1a4e6df44a86a23adce11a83c23d
Source dataset
uspto-grants-2014_08
Patent number
US08802674B2

Reaction notes

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