Water → HCID 59244400, compound

HRID 912385Notes

Reaction equation

HRID 912385 reaction equation
Cl[C:2]1[C:3]2[CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:7]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[N:8]1([C:6]2[N:7]=[C:2]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[C:3]3[CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[C:4]=3[N:5]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59244794HCID 59244794, compound

Product 1

HCID 59244400HCID 59244400, compoundYield 112.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-(4-Chloro-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-ethanone (J-01-D, 217 mg), 4-(4,4,5,5-tetramethyl-[1,3]dioxaborolan-2-yl)-pyridine (189 mg), palladium acetate (8.6 mg), S-Phos (32 mg) and potassium phosphate (326 mg) were suspended in DMF (7.6 ml), followed by stirring at 100° C. for 3 hours. To the reaction mixture, water (50 ml) was added, followed by extraction five times with ethyl acetate/THF (40 ml/10 ml). The combined extracts were washed with saturated aqueous sodium chloride solution, followed by drying over sodium sulfate. After the sodium sulfate was filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/0 to 50/1), to obtain the desired compound (D-323) as a pale yellow powder (282 mg, 100%).

Workup

  1. extractionfollowed by extraction five times with ethyl acetate/THF (40 ml/10 ml)
  2. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  3. dry with materialby drying over sodium sulfate
  4. filtrationAfter the sodium sulfate was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/0 to 50/1)

Sources & evidence

ORD record
ord-bc69495e0c644c93a7ed5831558fd820
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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