Methyl iodide → HCID 23353308, compound

HRID 235075Notes

Reaction equation

HRID 235075 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]2[S:10][CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].I[CH3:19]>C1COCC1.CO>[CH3:19][NH:3][C:4]1[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:6][C:7]2[CH:12]=[CH:11][S:10][C:8]=2[N:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23353262HCID 23353262, compound

Product 1

HCID 23353308HCID 23353308, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of neat NaH (0.82 g, 3.40 mmol) in 10 ml THF at -78° C. was canulated a cold (-78° C.) 20 ml THF solution of ethyl 3-aminothieno[2,3-b]pyrazine-2-carboxylate (0.690 g, 3.09 mmol). The reaction mixture was allowed to warm to rt, stir for 2 h and was then treated with iodomethane (0.460 g, 3.24 mmol). After stirring for 12 h at rt, the mixture was diluted with 5 ml MeOH and concentrated. Purification by column chromatography on silica gel eluting first with 10:1 then 5:1 hexanes:ethyl acetate gave the title compound (0.610 g, 84%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ1.40 (t, 3H), 3.60 (d, 3H), 4.36 (q, 2H), 7.48 (br s, 2H), 8.54 (d, 1H), 8.57 (d, 1H). MS (DCI/NH3) m/e 238 (M+H)+.

Workup

  1. stirringAfter stirring for 12 h at rt
  2. concentrationconcentrated
  3. customPurification by column chromatography on silica gel eluting first with 10:1

Sources & evidence

ORD record
ord-ea02ec4e0000439794f8f1cc49299626
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

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