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Triethylamine → 3-Amino-5-(2-methoxy-vinyl)-pyrazine-2-carboxylic acid methyl ester

HRID 1752502
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HRID 1752502 반응식
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([CH2:12][CH:13](OC)[O:14][CH3:15])=[CH:7][N:6]=1)=[O:4].CCN(CC)CC.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([CH:12]=[CH:13][O:14][CH3:15])=[CH:7][N:6]=1)=[O:4]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 86689170HCID 86689170, 화합물

생성물 1

HCID 780595033-Amino-5-(2-methoxy-vinyl)-pyrazine-2-carboxylic acid methyl ester수율 215.2%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 3-amino-5-(2,2-dimethoxy-ethyl)-pyrazine-2-carboxylic acid methyl ester (300 mg, 1.244 mmol) and Et3N (1.213 ml, 8.70 mmol) in DCM (10 ml) at −10° C. was added dropwise trimethylsilyl trifluoromethanesulfonate (0.809 ml, 4.48 mmol). The reaction mixture was stirred at room temperature for 100 min. A saturated solution of NaHCO3 was added and the mixture was extracted twice with DCM. The combined organic layers were washed with NH4Cl solution and brine, dried with Na2SO4, filtered and concentrated under reduced pressure to obtain a brown oil (560 mg). The resulting crude material (mixture of E and Z) was directly used in the next step without further purification.

후처리

  1. extractionthe mixture was extracted twice with DCM
  2. washThe combined organic layers were washed with NH4Cl solution and brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b451c0fb991341f4a4401020f18c8741
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09163011B2

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