Toluene → HCID 23353221, compound

HRID 235073Notes

Reaction equation

HRID 235073 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[S:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:26]1(C)[CH:31]=CC=C[CH:27]=1.IC(C)C>C1COCC1.CCO>[CH:26]([NH:1][C:2]1[N:7]=[C:6]2[S:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:31])[CH3:27]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6362Isopropyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 23353262HCID 23353262, compound

Product 1

HCID 23353221HCID 23353221, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 3-aminothieno[2,3-b]pyrazine-2-carboxylate (0.500 g, 2.24 mmol) was dissolved in 15 ml THF under nitrogen. The solution was cooled to -78° C and dropwise treated with 4.9 ml 0.5M KHMDS in toluene (2.46 mmol). The resulting purple reaction mixture was allowed to warm to rt, treated with 2-iodopropane (0.46 s g, 2.69 mmol) and then brought to reflux for 48h. After the addition of 1 ml EtOH, the reaction mixture was concentrated and applied directly to a silica gel column. Elution with a solvent gradient from 10:1 to 4:1 hexanes: ethyl acetate gave the title compound (0.210 g, 35%). 1H NMR (300 MHz, CDCl3) δ1.30 (d, 6H), 1.40 (t, 3H), 4.37 (q, 2H), 5.27 (dh, 1H), 7.42 (br d, 1H), 8.55 (d, 1H), 8.58 (d, 1H). MS (DCI/NH3) m/e 266 (M+H).

Workup

  1. temperatureto warm to rt
  2. temperatureto reflux for 48h
  3. concentrationthe reaction mixture was concentrated
  4. washElution with a solvent gradient from 10:1 to 4:1 hexanes

Sources & evidence

ORD record
ord-1c87af0b72fa49e3875185d10a10a988
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

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