Triethylamine → HCID 22347523, compound

HRID 897148Notes

Reaction equation

HRID 897148 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4]2[N:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:3]1=2.[C:13](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:14].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4]2[N:8]=[C:9]([CH2:12][CH2:13][OH:14])[CH:10]=[CH:11][C:3]1=2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 219345911,6-Dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 22347523HCID 22347523, compoundYield 118.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,6-dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (1.14 g, 7 mmol), di-tert-butyl dicarbonate (2.29 g, 10.5 mmol), DMAP (100 mg) and triethylamine (1.46 mL, 10.5 mmol) in 30 mL THF was refluxed 72 hours under N2. The reaction mixture was allowed to cool to room temperature and diluted with ethyl acetate. The mixture was washed with brine, dried over Na2SO4. After filtration and concentration at reduced pressure, the crude mixture was purified by flash chromatography on silica gel (40% EA/Hex) to afford the desired product (1.6 g, 90% yield) as yellow oil. H NMR (400 MHz, CDCl3) δ 1.51 (s, 9H), 2.40 (s, 3H), 2.90 (s, 3H), 3.28 (t, 2H), 3.83 (m, 2H), 6.78 (d, 1H), 6.83(d, 2H). Step 6. Synthesis of tert-butyl 6-(2-ethoxy-2-oxoethyl)-1-methyl-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxylate.

Workup

  1. washThe mixture was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and concentration at reduced pressure
  4. customthe crude mixture was purified by flash chromatography on silica gel (40% EA/Hex)

Sources & evidence

ORD record
ord-5eb9df62633047c9a11865c62c4e596a
Source dataset
uspto-grants-2005_07
Patent number
US06921767B2

Reaction notes

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