Triphenylphosphine → HCID 45258863, compound

HRID 912389Notes

Reaction equation

HRID 912389 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][NH:27][C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[Cl:41][C:42]1[CH:47]=[C:46](I)[CH:45]=[CH:44][N:43]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:41][C:42]1[CH:47]=[C:46]([N:27]2[C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=[C:15]([C:12]4[CH:11]=[N:10][C:9]([N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:40][CH:39]=5)[CH2:30][C:31]5[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=5)=[N:14][CH:13]=4)[C:16]=3[CH2:29][CH2:28]2)[CH:45]=[CH:44][N:43]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 15165112-Chloro-4-iodopyridineHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

Product 1

HCID 45258863HCID 45258863, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (1.65 g) was suspended in dimethylformamide (20 ml), followed by addition of 2-chloro-4-iodopyridine (805 mg), palladium acetate (35 mg), triphenylphosphine (81 mg) and potassium phosphate (1.95 g), and argon gas was blown for 10 minutes while irradiating ultrasonic wave. The reaction mixture was stirred at 100° C. for 1 hour, and cooled to room temperature, followed by addition of water (50 ml). The mixture was extracted with ethyl acetate (100 ml) and dichloromethane (100 ml), and the combined organic layers were washed with brine, followed by drying over sodium sulfate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=50/1), followed by suspension of the residue in ethyl acetate/hexane (10 ml/50 ml). The precipitate was filtered, and washed with hexane, followed by drying under reduced pressure, to obtain a yellow powder (1.75 g, 88%).

Workup

  1. customwhile irradiating ultrasonic wave
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate (100 ml) and dichloromethane (100 ml)
  4. washthe combined organic layers were washed with brine
  5. dry with materialby drying over sodium sulfate
  6. filtrationAfter filtering off the drying agent
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=50/1)
  9. additionfollowed by suspension of the residue in ethyl acetate/hexane (10 ml/50 ml)
  10. filtrationThe precipitate was filtered
  11. washwashed with hexane
  12. customby drying under reduced pressure

Sources & evidence

ORD record
ord-f683a35e24d9491e8c0f3d854d960cc6
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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