Potassium Carbonate → HCID 58765530, compound

HRID 860041Notes

Reaction equation

HRID 860041 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].B1C2CCCC1CCC2.Cl[C:20]1[N:25]=[C:24]([NH2:26])[N:23]=[C:22]([NH2:27])[CH:21]=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>[CH2:8]([O:7][C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH2:5][C:20]1[N:25]=[C:24]([NH2:26])[N:23]=[C:22]([NH2:27])[CH:21]=1)[CH3:9]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 674322,4-Diamino-6-chloropyrimidineHCID 74786Ethyl 4-pentenoateHCID 789669-Borabicyclo(3.3.1)nonane

Product 1

HCID 58765530HCID 58765530, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

Ethyl 4-pentenoate (4.93 gm, 38.4 mmol) was treated with 9-BBN (92.2 mL, 46.1 mmol; 0.5M in THF) at room temperature for 16 hours. To this solution was added Pd(OAc)2 (863 mg, 3.84 mmol), 6-chloro-2,4-diaminopyrimidine (2-1, 5.0 g, 34.6 mmol), K2CO3 (7.95 g, 57.6 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (2.13 g, 3.84 mmol) and DMF (100 mL). The mixture was degassed with argon for 10 minutes then heated to 90° C. for 24 hours. The reaction mixture was cooled and stirred with ethanolamine (10 mL) for 1 hour. The volatiles were removed in vacuo and the black tarry residue was partitioned between water and EtOAc. After extraction with EtOAc (4×), the organic layers were washed with water (4×), then brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography (5% MeOH in CHCl3) afforded the title compound 2-2 as an oil.

Workup

  1. customThe mixture was degassed with argon for 10 minutes
  2. temperatureThe reaction mixture was cooled
  3. customThe volatiles were removed in vacuo
  4. customthe black tarry residue was partitioned between water and EtOAc
  5. extractionAfter extraction with EtOAc (4×)
  6. washthe organic layers were washed with water (4×)
  7. dry with materialbrine, dried (MgSO4)
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-5598bed4a6234151a378c0d39cdd8952
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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