Potassium Phosphate, Tribasic → HCID 59244873, compound

HRID 912387Notes

Reaction equation

HRID 912387 reaction equation
COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O.[NH2:39][C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][CH:45]=1.Cl[C:50]1[C:51]2[CH2:64][CH2:63][N:62]([C:65]3[CH:70]=[CH:69][N:68]=[CH:67][CH:66]=3)[C:52]=2[N:53]=[C:54]([N:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)[N:55]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C)C=O>[N:56]1([C:54]2[N:55]=[C:50]([C:42]3[CH:41]=[C:40]([NH2:39])[CH:45]=[CH:44][CH:43]=3)[C:51]3[CH2:64][CH2:63][N:62]([C:65]4[CH:66]=[CH:67][N:68]=[CH:69][CH:70]=4)[C:52]=3[N:53]=2)[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 143894233-Aminophenylboronic acid monohydrateHCID 592447084-chloro-2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 59244873HCID 59244873, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Palladium acetate (9 mg, 10 mol %), S-Phos (33 mg, 20 mol %), potassium phosphate (340 mg, 4 equivalents) and 3-aminophenylboronic acid hydrate (189 mg, 3 equivalents) were weighed in a two-neck flask equipped with Dimroth condenser, and heated with a drier under reduced pressure, followed by several repetitive argon substitution. A dimethylformamide solution (4 ml) of 4-chloro-2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine was added with a syringe, followed by stirring at 110° C. for 10 hours. The reaction mixture was added to water, followed by extraction twice with ethyl acetate, and the organic layer was washed with brine, and subsequently dried over sodium sulfate. The drying agent was filtered off, followed by concentration under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/ammonia-methanol), to obtain the desired compound (yellow powder, 62 mg, 41%) was obtained.

Workup

  1. customequipped with Dimroth condenser
  2. temperatureheated with a drier under reduced pressure
  3. extractionfollowed by extraction twice with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialsubsequently dried over sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationfollowed by concentration under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/ammonia-methanol)

Sources & evidence

ORD record
ord-7f035f89fd814dfea6d50dfedae5b20c
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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