Triacetoxyperiodinane → Methyl 4-(3-oxo-8-azabicyclo[3.2.1]octan-8-yl)-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate

HRID 928597Notes

Reaction equation

HRID 928597 reaction equation
[OH:1][CH:2]1[CH2:8][CH:7]2[N:9]([C:10]3[C:11]4[C:18]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)=[C:17]([C:25]([O:27][CH3:28])=[O:26])[S:16][C:12]=4[N:13]=[CH:14][N:15]=3)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][CH:4]2[N:9]([C:10]3[C:11]4[C:18]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)=[C:17]([C:25]([O:27][CH3:28])=[O:26])[S:16][C:12]=4[N:13]=[CH:14][N:15]=3)[CH:7]([CH2:6][CH2:5]2)[CH2:8]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 89579774Methyl 4-(3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 89579504Methyl 4-(3-oxo-8-azabicyclo[3.2.1]octan-8-yl)-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-(3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate (0.940 g, 2.38 mmol) in DCM (100 mL) at room temperature was added Dess-Martin Periodinane (1.310 g, 3.094 mmol) in one portion and the reaction left to stir overnight. The reaction was filtered and the filtrate washed with saturated sodium bicarbonate and brine, the organic layer dried over sodium sulphate, filtered and concentrated under reduced pressure to afford methyl 4-(3-oxo-8-azabicyclo[3.2.1]octan-8-yl)-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate which was used without further purification (0.935 g, 100%). LCMS: Rt=4.46, 394 (M+1).

Workup

  1. waitthe reaction left
  2. filtrationThe reaction was filtered
  3. washthe filtrate washed with saturated sodium bicarbonate and brine
  4. dry with materialthe organic layer dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40ebebe28ab24e698d14181730b0f85d
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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