Potassium Carbonate → (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(4'-dimethylamino-biphenyl-3-yl)methanone

HRID 916770Notes

Reaction equation

HRID 916770 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=3)=[O:12])=[CH:9][N:8]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:25][N:26]([CH3:36])[C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.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>[Cl:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[C:15]([C:30]4[CH:31]=[CH:32][C:27]([N:26]([CH3:36])[CH3:25])=[CH:28][CH:29]=4)[CH:16]=[CH:17][CH:18]=3)=[O:12])=[CH:9][N:8]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27343444-(Dimethylamino)phenylboronic acidHCID 86760548(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-iodo-phenyl)-methanone

Product 1

HCID 86760550(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(4'-dimethylamino-biphenyl-3-yl)methanoneYield 47%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-iodo-phenyl)-methanone (100 mg, 0.22 mmol), 4-(dimethylamino)Phenyl boronic acid (42.9 mg, 0.26 mmol), PdCl2(PPh3)2 (7.7 mg, 0.011 mmol), and K2CO3 (45.6 mg, 0.33 mmol) in 1,4-dioxane (3 mL) and water (0.5 mL) was heated to 90° C. After 24 h the reaction was diluted with EtOAc and filtered through celite. The filtrate was washed with water, dried over Na2SO4, and concentrated. Purification by flash column chromatography (hexanes/ethyl acetate 8:2) afforded the title compound as a white solid (46 mg, 47%). MS: 445.1/447.1 (MH+); HPLC Rf: 8.05 min. (HPLC method 4).

Workup

  1. filtrationfiltered through celite
  2. washThe filtrate was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (hexanes/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-f3056eff86ce46bc949883f25a951ed7
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

Loading…