Sodium Carbonate → Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate

HRID 1184817노트

반응식

HRID 1184817 반응식
Cl[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16]([O:18][C:19](=[O:22])[CH2:20][SH:21])[CH3:17]>C(O)C>[NH2:9][C:8]1[C:3]2[C:2](=[N:7][CH:6]=[CH:5][N:4]=2)[S:21][C:20]=1[C:19]([O:18][CH2:16][CH3:17])=[O:22]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 12185Ethyl ThioglycolateHCID 2924653-Chloropyrazine-2-carbonitrile

생성물 1

HCID 2820821Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate수율 68.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 3-chloropyrazine-2-carbonitrile (17.9 g, 128 mmol), sodium carbonate (17.7 g, 167 mmol) and ethyl-2-mercaptoacetate (18.4 mL, 167 mmol) in ethanol (120 mL) was heated to reflux for 4.5 h. Quenched with water (1.5 L) and stirred for 30 min. The resulting precipitate was collected and washed with water. The residue was dissolved in diethyl ether and a black precipitate was filtrated off. Ether was evaporated to give pure compound ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (19.6 g, 68.5%). 1H-NMR (400 MHz, CDCl3) 1.42 (t, J=7.2 Hz, 3H), 4.40 (q, J=7.2 Hz, 2H), 6.19 (br s, 1H), 8.58 (d, J=2.2 Hz, 1H), 8.63 (d, J=2.2 Hz, 1H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 h
  3. customQuenched with water (1.5 L)
  4. customThe resulting precipitate was collected
  5. washwashed with water
  6. dissolutionThe residue was dissolved in diethyl ether
  7. filtrationa black precipitate was filtrated off
  8. customEther was evaporated

출처 및 근거

ORD 기록
ord-d6aa3e1b4e374f28ba77786de6b250da
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669256B2

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