Potassium Carbonate → HCID 21113160, compound

HRID 1767041Notes

Reaction equation

HRID 1767041 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([C:13]#[C:14][Si](C)(C)C)[CH:7]=[CH:8][N:9]=2)[N:4]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:13]([C:6]1[CH:7]=[CH:8][N:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]2)#[CH:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 211131562-Methoxy-8-trimethylsilanylethynyl-[1,5]naphthyridine

Product 1

HCID 21113160HCID 21113160, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-Methoxy-8-trimethylsilanylethynyl-[1,5] naphthyridine in methanol (80 mL) was treated with potassium carbonate (4.49 g, 32 mmole) and stirred 1.5 hrs. The reaction mixture was concentrated to dryness, redissolved in ethyl acetate, and partitioned with brine. The biphasic mixture was filtered to facilitate separation. Organic layer was dried over sodium sulfate, filtered, concentrated and chromatographed in 1:1 ethyl acetate:hexane to give the product as a cream colored solid. δH (CDCl3, 400 MHz), 8.73 (d, J=4Hz, 1 H), 8.20 (d, J=9 Hz, 1 H), 7.68 (d, J=4 Hz, 1H), 7.16 (d, J=9 Hz, 1 H), 4.15 (s, 3H), 3.67 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionredissolved in ethyl acetate
  3. custompartitioned with brine
  4. filtrationThe biphasic mixture was filtered
  5. customseparation
  6. dry with materialOrganic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed in 1:1 ethyl acetate
  10. customhexane to give the product as a cream

Sources & evidence

ORD record
ord-2abc1939da45454d87aac615c2593c7b
Source dataset
uspto-grants-2007_06
Patent number
US07232832B2

Reaction notes

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