2-Bromoethyl methyl ether → Ethyl 7-(N-(2-methoxyethyl)amino)thieno[2,3-b]pyrazine-6-carboxylate

HRID 1003396Notes

Reaction equation

HRID 1003396 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:26][O:27][CH2:28][CH2:29]Br>C1COCC1>[CH3:26][O:27][CH2:28][CH2:29][NH:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 2820821Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 18796873Ethyl 7-(N-(2-methoxyethyl)amino)thieno[2,3-b]pyrazine-6-carboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-amino-thieno[2,3-b]pyrazine-6-carboxylate (1.0 g g, 4.48 mmol) prepared by the method of Schneller and Clough, J. Het. Chem., 12: 513 (1975), was treated with potassium bis(trimethylsilyl)amide (0.5M in toluene, 8.96 ml) in 15 ml THF at -70° C., and allowed to warm to room temperature. 2-Bromoethyl methyl ether (0.454 ml, 4.70 mmol) was added, and the reaction was stirred under N2 at 60° C. overnight. The mixture was cooled and evaporated, then purified by column chromatography on silica gel eluting with 1:9 ethyl acetate:hexanes to yield 0.640 g (51%) of the title compound as a yellow solid: 1H NMR (300 MHz, DMSO-d6) d 1.32 (t, 3H), 3.3 (s, 3H), 3.56 (t, 2H), 4.25 (q, 2H), 4.32 (t, 2H), 7.70 (br t, 1H), 8.76 (s, 1H), 8.77 (s, 1H); MS (DCI/NH3) m/e 282 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated
  3. custompurified by column chromatography on silica gel eluting with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-ada9b198fa9a4365b0f468051cd33493
Source dataset
uspto-grants-2000_04
Patent number
US06046207

Reaction notes

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