2-Methyl-2-butene → HCID 11689341, compound

HRID 1821646Notes

Reaction equation

HRID 1821646 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:24]=3)[CH:22]=[O:23])[N:15]=2)[NH:10][C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.[O-:33]Cl=O.[Na+]>CC(O)(C)C>[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:24]=3)[C:22]([OH:33])=[O:23])[N:15]=2)[NH:10][C:9]1=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 105532-Methyl-2-buteneHCID 11653391HCID 11653391, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 11689341HCID 11689341, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 5-(3-Benzyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)-2-methoxybenzaldehyde (296 mg, 0.82 mmol) in t-BuOH (18.2 mL) was sequentially added saturated aqueous NaH2PO4 solution (4.1 mL), 2-methyl-2-butene (2M in THF, 3.92 mL) and NaClO2 (114.8 mg). The mixture was stirred at room temperature for one hour, and then concentrated under reduced pressure. The residue thus obtained was purified by column chromatography [silica gel; MeOH/DCM (1:9)] to give the product as white powder (244 mg, 65%). 1H NMR (400 MHz, DMSO): δ 8.44 (s, 1H), 8.19 (s, 1H), 8.08 (d, J=9.2 Hz, 1H), 7.40-7.26 (m, 5H), 7.18 (d, J=8.8 Hz, 1H), 5.05 (s, 2H), 3.84 (s, 3H). MS: 377.0 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by column chromatography [silica gel; MeOH/DCM (1:9)]

Sources & evidence

ORD record
ord-94a6eef883f046dd9092fdaf8ec36025
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

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