Benzyl Bromide → HCID 23353357, compound

HRID 235076Notes

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].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([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])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 24758Sodium hydride

HCID 23353262HCID 23353262, compound

Product 1

HCID 23353357HCID 23353357, compoundYield 62%

Procedure

Ethyl 3-aminothieno[2,3-b]pyrazine-2-carboxylate (0.450 g, 2.02 mmol) was treated with neat NaH (0.058 g, 2.42 mmol) and benzyl bromide (0.380 g, 2.22 mmol) as described in Example 94A. Purification by column chromatography on silica gel eluting with a solvent gradient from 10:1 to 3:1 hexanes:ethyl acetate gave the title compound (0.39 g, 62%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ1.39 (t, 3H), 4.37 (q, 2H), 5.38 (d, 2H), 7.19-7.42 (m, 5H), 7.88 (br t, 1H), 8.55 (m, 2H). MS (DCI/NH3) m/e 3 14 (M+H)+.

Workup

customPurification by column chromatography on silica gel eluting with a solvent gradient from 10:1 to 3:1 hexanes

Sources & evidence

ORD record: ord-06e04dace9cc45f9aacbdc0df4809463
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05597823

Reaction notes

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