Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 59312287, compound

HRID 2077047Notes

Reaction equation

HRID 2077047 reaction equation
[CH2:1]([N:8]([CH3:28])[C:9]1[NH:10][C:11](=[O:27])[C:12]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14][C:13]=2[N:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.[CH3:34][O+](C)C>C(Cl)Cl>[CH2:1]([N:8]([CH3:28])[C:9]1[N:10]=[C:11]([O:27][CH3:34])[C:12]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14][C:13]=2[N:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 136058099HCID 136058099, compound

Product 1

HCID 59312287HCID 59312287, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-[benzyl(methyl)amino]-4-oxo-3,4,5,6,8,9-hexahydro-7H-pyrimido[4,5,d]azepine-7-carboxylate of Preparation 16, Step A (70 mg, 0.19 mmol) in DCM (2 ml) was added trimethyloxonium tetrafluoroborate (3 eq., 84.1 mg, 0.57 mmol) and the mixture was stirred for 2 h. The combined organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with ethyl actate/pentane (1:3 to 1:1). The relevant fractions were combined and concentrated in vacuo to afford the title compound as a colourless oil (31 mg, 41% yield).

Workup

  1. dry with materialdried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluting with ethyl actate/pentane (1:3 to 1:1)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e5f8fe1fe774085995f1b3c45717033
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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