Dichloromethane → ((3aR,4R,6R,6aR)-2,2-Dimethyl-6-{6-[3-(1H-pyrazol-1-yl)phenyl]-9H-purin-9-yl}-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetate

HRID 552703Notes

Reaction equation

HRID 552703 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:13]2[C@@H:9]([O:10][C:11]([CH3:15])([CH3:14])[O:12]2)[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3Br)[O:7]1)(=[O:3])[CH3:2].[N:26]1([C:31]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=2)[CH:30]=[CH:29][CH:28]=[N:27]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].ClCCl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:13]2[C@@H:9]([O:10][C:11]([CH3:15])([CH3:14])[O:12]2)[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)[CH:36]=2)[O:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 16640530(3-(1H-pyrazol-1-yl)phenyl)boronic acidHCID 86607305[(3aR,4R,6R,6aR)-6-(6-Bromo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate

Product 1

HCID 67165486((3aR,4R,6R,6aR)-2,2-Dimethyl-6-{6-[3-(1H-pyrazol-1-yl)phenyl]-9H-purin-9-yl}-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetateYield 53%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
150 °C

Procedure

[(3aR,4R,6R,6aR)-6-(6-Bromo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate (0.1 g, 0.242 mmol), 3-(1-H-pyrazole-1-yl)phenylboronic acid (0.137 g, 0.726 mmol), potassium phosphate (0.154 g, 0.726 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex dichloromethane (1:1) (0.040 g, 0.048 mmol) were placed in an oven-dried microwave vial and degassed with argon. Anhydrous dioxane (1.5 mL) was added and the reaction was heated to 150° C. for ten minutes in the microwave. The mixture was filtered through a pad of Celite washing with dichloromethane then concentrated. The residue was taken up in dichloromethane and purified on a prep plate using 60% ethyl acetate/hexanes as developing solvent to give the title compound as a yellow solid (0.061 g 53%).

Workup

  1. customdegassed with argon
  2. additionAnhydrous dioxane (1.5 mL) was added
  3. filtrationThe mixture was filtered through a pad of Celite
  4. washwashing with dichloromethane
  5. concentrationthen concentrated
  6. custompurified on a prep plate

Sources & evidence

ORD record
ord-12998207a6314d17ba318117bb96baed
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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