Potassium Carbonate → HCID 69667060, compound
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[CH:25]=[C:24]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[N:23]=[C:22]([NH:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[N: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:21]=[C:22]([NH:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[N:23]=[C:24]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH:25]=1)[CH3:9]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Ethyl 4-pentenoate (1.0 g, 7.8 mmol) was treated with 9-BBN (18.72 mL, 9.36 mmol; 0.5M in THF) at room temperature for 16 hours. To this solution was added Pd(OAc)2 (175 mg, 0.78 mmol), pyrimidine 7-2 (2.44 mg, 7.8 mmol), K2CO3 (2.15 g, 15.6 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (DPPF) (433 mg, 0.78 mmol) and DMF (25 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 ethanolamine (10 mL) for 3 hours. The mixture was partitioned between saturated NaHCO3 and EtOAc, washed with brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography (hexane:EtOAc 2:1) afforded the title compound 7-3 as a solid.
Workup
- customThe mixture was degassed with argon for 10 minutes
- temperatureThe reaction mixture was cooled
- customThe mixture was partitioned between saturated NaHCO3 and EtOAc
- washwashed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customPurification by silica gel chromatography (hexane:EtOAc 2:1)
Sources & evidence
- ORD record
- ord-eb7c87ce7bfb4dcc882e4b364b2287a3
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06693101B2
Reaction notes
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