Tetrahydrofuran → 3-(2-{(3aS,5R,6S,6aS)-2,2-dimethyl-5-[2-(4-pyrimidin-5-ylphenyl)ethyl]tetrahydrofuro[2,3-d][1,3]dioxol-6-yl}ethyl)-1,2,3-benzotriazin-4(3H)-one

HRID 83997Notes

Reaction equation

HRID 83997 reaction equation
[CH3:1][C:2]1([CH3:37])[O:6][C@@H:5]2[O:7][C@H:8](/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:32]=[N:33][CH:34]=[N:35][CH:36]=4)=[CH:27][CH:26]=3)[C@H:9]([CH2:10][CH2:11][N:12]3[C:17](=[O:18])[C:16]4[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=4[N:14]=[N:13]3)[C@@H:4]2[O:3]1.O1CCCC1.[H][H]>[Pd].CO>[CH3:1][C:2]1([CH3:37])[O:6][C@@H:5]2[O:7][C@H:8]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]4[CH:32]=[N:33][CH:34]=[N:35][CH:36]=4)=[CH:29][CH:30]=3)[C@H:9]([CH2:10][CH2:11][N:12]3[C:17](=[O:18])[C:16]4[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=4[N:14]=[N:13]3)[C@@H:4]2[O:3]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 671828423-(2-{(3aS,5R,6S,6aS)-2,2-dimethyl-5-[(E)-2-(4-pyrimidin-5-ylphenyl)vinyl]tetrahydrofuro[2,3-d][1,3]dioxol-6-yl}ethyl)-1,2,3-benzotriazin-4(3H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 687630853-(2-{(3aS,5R,6S,6aS)-2,2-dimethyl-5-[2-(4-pyrimidin-5-ylphenyl)ethyl]tetrahydrofuro[2,3-d][1,3]dioxol-6-yl}ethyl)-1,2,3-benzotriazin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of the compound obtained from step k above (0.3 g) in a solvent mixture of tetrahydrofuran:methanol (10 mL, 1:1), 10% palladium on charcoal (0.15 g) was added at room temperature and the reaction mixture was hydrogenated with hydrogen at 35 psi for 4 hours in a Paar apparatus. The reaction mixture was filtered through a celite pad and the residue was washed with methanol. The filtrate was concentrated to afford the title compound (0.3 g).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe residue was washed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0a3ea3f76e504da0adbf573e11a8d8f9
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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