Water → HCID 89442540, compound

HRID 632720Notes

Reaction equation

HRID 632720 reaction equation
Br[C:2]1[C:3]([NH2:29])=[N:4][CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH2:15][N:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]1.[C:30]1([CH3:36])C=CC=C[CH:31]=1.O.C1([B-](F)(F)F)CC1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:36]1([C:2]2[C:3]([NH2:29])=[N:4][CH:5]=[N:6][C:7]=2[N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[CH2:15][N:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]2)[CH2:30][CH2:31]1

Participants

8

Reactant 6

HCID 962WaterHCID 1140TolueneHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23697338Potassium cyclopropyltrifluoroborateHCID 89442508HCID 89442508, compound

Product 1

HCID 89442540HCID 89442540, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

In a microwave vial containing 5-bromo-6-{4-[2-dimethylamino-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-pyrimidin-4-ylamine (84.00 mg; 0.18 mmol; 1.00 eq.) in toluene (3.00 ml; 28.23 mmol; 159.07 eq.) and water (0.30 ml; 16.65 mmol; 93.84 eq.) was added palladium(ii) acetate (3.98 mg; 0.02 mmol; 0.10 eq.), potassium cyclopropyltrifluoroborate (52.52 mg; 0.35 mmol; 2.00 eq.), cesium carbonate (127.21 mg; 0.39 mmol; 2.20 eq.) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (20.54 mg; 0.04 mmol; 0.20 eq.). The mixture was microwaved at 125° C. for 30 min before it was filtered the desired product was purified with Waters prep-HPLC. LC-MS: (M+1=435, obsd.=435)

Workup

  1. customThe mixture was microwaved at 125° C. for 30 min before it
  2. filtrationwas filtered the desired product
  3. customwas purified with Waters prep-HPLC

Sources & evidence

ORD record
ord-4909cb2f8aa347a08e159d34eeb81c99
Source dataset
uspto-grants-2016_04
Patent number
US09321760B2

Reaction notes

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