Methanol → HCID 59541847, compound

HRID 2388313Notes

Reaction equation

HRID 2388313 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[N:16]=[C:15]([NH2:17])[CH:14]=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:20]I.CO>CN(C=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[N:16]=[C:15]([NH:17][CH3:20])[CH:14]=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59541755HCID 59541755, compound

Product 1

HCID 59541847HCID 59541847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-pyridin-2-ylamine (as prepared in Example 22, Step A, 2.5 g, 10.8 mmol) in DMF (10 mL) was treated with NaH (Aldrich, 95%, 550 mg, 21.6 mmol) at 0° C. The reaction was stirred for 20 min. and MeI (Aldrich, 810 μL, 12 mmol) was slowly added. The reaction was warmed to room temperature over 2 hours. MeOH (˜1 mL) was added to quench the extra NaH. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow oil, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as white solid.

Workup

  1. customto quench the extra NaH
  2. customThe reaction solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil, which
  8. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-1dc017c960c14725be9a75fb98058ca0
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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