Potassium Phosphate, Tribasic → HCID 67165409, compound
Reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:43]([O:46][C@H:47]1[CH2:51][C@H:50]([N:52]2[CH:60]=[N:59][C:58]3[C:53]2=[N:54][CH:55]=[N:56][C:57]=3Br)[O:49][C@@H:48]1[CH2:62][O:63][Si:64]([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65])(=[O:45])[CH3:44]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:43]([O:46][C@H:47]1[CH2:51][C@H:50]([N:52]2[CH:60]=[N:59][C:58]3[C:53]2=[N:54][CH:55]=[N:56][C:57]=3[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:49][C@@H:48]1[CH2:62][O:63][Si:64]([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65])(=[O:45])[CH3:44]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
A flame dried flask was charged with Pd(OAc)2 (0.0185 g, 0.0823 mmol), 2-(dicyclohexylphosphino)biphenyl (0.0433 g, 0.123 mmol), phenyl boronic acid (0.151 g, 1.23 mmol), and K3PO4 under an atmosphere of argon. A solution of (2R,3S,5R)-5-(6-bromo-9H-purin-9-yl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-3-yl acetate (0.388 g, 0.823 mmol) in dry dioxane (5.49 mL) was added to the mixture and the solution was stirred at 90° C. overnight. The reaction mixture was filtered through celite with CH2Cl2, concentrated and purified by flash chromatography (10 to 30% EtOAc/hexanes) to afford the title compound as a clear oil (0.247 g, 64%).
Workup
- customA flame dried flask
- filtrationThe reaction mixture was filtered through celite with CH2Cl2
- concentrationconcentrated
- custompurified by flash chromatography (10 to 30% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-b92ea10274ac4708946f23183378fd41
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951810B2
Reaction notes
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