Potassium Carbonate → HCID 70091948, compound

HRID 2187393Notes

Reaction equation

HRID 2187393 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([C:14]1[CH:15]=[N:16][C:17]([CH3:20])=[N:18][CH:19]=1)[CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH:11]=[CH2:12])[CH3:2].B1C2CCCC1CCC2.Cl[C:32]1[N:37]=[C:36]([NH2:38])[N:35]=[C:34]([NH2:39])[CH:33]=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CN(C=O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([C:14]1[CH:15]=[N:16][C:17]([CH3:20])=[N:18][CH:19]=1)[CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH2:12][C:32]1[N:37]=[C:36]([NH2:38])[N:35]=[C:34]([NH2:39])[CH:33]=1)[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 674322,4-Diamino-6-chloropyrimidineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 54012975HCID 54012975, compound

Product 1

HCID 70091948HCID 70091948, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The ester 15-5 (400 mg, 1.38 mmol) was treated with 9-BBN (8.28 mL, 4.14 mmol; 0.5M in TBF) at room temperature for 16 hours. To this solution was added Pd(OAc)2 (31 mg, 0.14 mmol), 6-chloro-2,4-diaminopyrimidine (219 mg, 1.52 mmol), K2CO3 (381 mg, 2.75 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (76 mg, 0.14 mmol) and DMF (15 mL). The mixture was degassed with argon for 10 minutes then heated to 80° C. for 24 hours. The reaction mixture was cooled and stirred with ethanolarnine (5 mL) for 2 hours. The mixture was partitioned between 1N HCl and EtOAc. The aqueous layer was made basic with K2CO3 and extracted with EtOAc (5×). The organic layers were washed with brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography (20% MeOH in CHCl3) afforded the title compound 15-6 as an oil.

Workup

  1. customThe mixture was degassed with argon for 10 minutes
  2. temperatureThe reaction mixture was cooled
  3. customThe mixture was partitioned between 1N HCl and EtOAc
  4. extractionextracted with EtOAc (5×)
  5. washThe organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (20% MeOH in CHCl3)

Sources & evidence

ORD record
ord-17b9e270c9d343c3ad78b8d04dee9af3
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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