HCID 86677188, compound → HCID 86677190, compound

HRID 2405896Notes

Reaction equation

HRID 2405896 reaction equation
[Si:1]([C:8]1[C:13]([F:14])=[C:12]([F:15])[N:11]=[C:10]([CH:16]([C:18]2[C:19]([Cl:25])=[N:20][CH:21]=[N:22][C:23]=2[Cl:24])[OH:17])[C:9]=1[F:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[Si:1]([C:8]1[C:13]([F:14])=[C:12]([F:15])[N:11]=[C:10]([C:16]([C:18]2[C:19]([Cl:25])=[N:20][CH:21]=[N:22][C:23]=2[Cl:24])=[O:17])[C:9]=1[F:26])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86677188HCID 86677188, compound

Product 1

HCID 86677190HCID 86677190, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of [4-[tert-butyl(dimethyl)silyl]-3,5,6-trifluoro-2-pyridyl]-(4,6-dichloropyrimidin-5-yl)methanol (1.21 g, 2.85 mmol) and Manganese (IV) oxide (3.72 g, 42.78 mmol) in DCM (53 mL) was stirred at ambient temperature for 5 days. After this time, further Manganese (IV) oxide (992 mg, 11.4 mmol) was added and stirred at ambient for 2 hours. The reaction mixture was filtered through a celite cartridge, washing through with DCM, and the filtrate concentrated in vacuo to leave the sub title product as a white solid (908 mg, 74.8% Yield). H1 NMR (400 MHz, DMSO) δ 9.15 (1H, s), 0.94 (9H, s) and 0.45 (6H, s).

Workup

  1. stirringstirred at ambient for 2 hours
  2. filtrationThe reaction mixture was filtered through a celite cartridge
  3. washwashing through with DCM
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-231cf03018f04f2d8f32541dd0200fd5
Source dataset
uspto-grants-2014_08
Patent number
US08809335B2

Reaction notes

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