HCID 18669678, compound → HCID 18669679, compound

HRID 1059003Notes

Reaction equation

HRID 1059003 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[CH:22]=4)[CH2:19][CH2:18][C:17](=[O:20])[CH:16]=[CH:15]3)=[CH:10][CH:9]=2)=[CH:4][N:3]=1>C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH:30]5[CH2:31][CH2:32][CH2:33][CH2:34]5)[CH:22]=4)[CH2:15][CH2:16][C:17](=[O:20])[CH2:18][CH2:19]3)=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 18669678HCID 18669678, compound

Product 1

HCID 18669679HCID 18669679, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 4-[4-(2-aminopyrimidin-5-yl)phenyl]-4-(3-cyclopentyloxy-4-methoxyphenyl)-2-cyclohexen-1-one (1.2 g, 2.63 mmol) in ethyl acetate (20 ml) with palladium on activated carbon (360 mg, 30% w/w) was stirred under hydrogen at atmospheric pressure for three days then filtered and the residue washed with dichloromethane. The combined organic solution was evaporated to afford the title compound as a gray solid (1.05 g, 88% crude yield). 1H-NMR (400 MHz, CDCl3): δ 8.51 (s, 2H), 7.44 (d, 2H, J=8.4), 7.38 (d, 2H, J=8.4), 6.89 (dd, 1H, J=8.4, J=2.2), 6.84 (d, 1H, J=8.4), 6.83 (d, 1H, J=2.2), 5.21 (s, 2H), 4.69 (m, 1H), 3.83(s, 3H), 2.64 (m, 4H), 2.48 (m, 4H). 1.81 (m, 6H), 1.57 (m, 2H).

Workup

  1. filtrationthen filtered
  2. washthe residue washed with dichloromethane
  3. customThe combined organic solution was evaporated

Sources & evidence

ORD record
ord-2f09fa62e24b4141b789a7cb4f226ee9
Source dataset
uspto-grants-2003_02
Patent number
US06518306B1

Reaction notes

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