Dimethylformamide → HCID 86712719, compound

HRID 1779083Notes

Reaction equation

HRID 1779083 reaction equation
[CH3:1][C:2]1[C:3]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][C:24]([O-:26])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.[CH3:27]N(C=O)C>CCN(CC)CC.[Pd]>[CH3:1][C:2]1[C:3]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][C:24]([O:26][CH3:27])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86712720HCID 86712720, compound

Product 1

HCID 86712719HCID 86712719, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

10% Pd/C (53% water; 0.020 g) was added to a solution of methyl 2-(2-((5-methyl-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-ylethynyl)phenyl)acetate (A115) (0.115 g, 0.318 mmol) in DMF (5 mL) and Et3N (0.5 mL) and the resulting suspension placed under a hydrogen atmosphere and stirred at room temperature for 18 hours. The mixture was filtered through Celite, washing with EtOAc (250 mL). The combined filtrates were washed with water (100 mL) then brine (100 mL) and the washing repeated 3 times. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure and the resulting oil purified by silica gel column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in hexanes) to give the title compound A116 as a yellow solid (0.097 g, 83%); 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.83 (s, 1H), 7.46 (s, 1H), 7.25-7.17 (m, 4H), 6.75 (s, 1H), 3.89 (s, 3H), 3.72 (s, 2H), 3.67 (s, 3H), 3.09 (dd, J=9.5, 6.3 Hz, 2H), 2.91 (dd, J=9.5, 6.4 Hz, 2H), 2.07 (s, 3H). LCMS-A: rt 5.160 min; m/z 366 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashing with EtOAc (250 mL)
  3. washThe combined filtrates were washed with water (100 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting oil purified by silica gel column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-23e66e66cab54ba6af2feaf7f6d8adb1
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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