Hydrazine → 3-Amino-6-chloro-5-hydrazino-pyrazine-2-carboxylic acid methyl ester

HRID 1274145

반응식

HRID 1274145 반응식
[NH2:1][C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][C:5]([Cl:9])=[C:6](Cl)[N:7]=1.[NH2:14][NH2:15].CO.C(Cl)Cl>C(O)(C)(C)C.CN(C=O)C>[CH3:13][O:12][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH:14][NH2:15])=[C:5]([Cl:9])[N:4]=1)=[O:11]

참가 물질

6

반응물 3

HCID 9321HydrazineHCID 73828Methyl 3-amino-5,6-dichloropyrazine-2-carboxylateHCID 21226129Dichloromethane methanol

생성물 1

HCID 541673563-Amino-6-chloro-5-hydrazino-pyrazine-2-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6386tert-Butanol용매

반응 조건

온도
25 °C

실험 절차

Methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.10 g, 5 mmol) was dissolved in 20 mL of tert-butyl alcohol and DMF (v/v; 1:1). Anhydrous hydrazine (0.18 mL, 5.5 mmol) and N,N'-diisopropylethyl amine (4.5 mL, 25 mmol) were then added sequentially at 25° C. The resulting mixture was stirred at 25° C. for 12 h. The reaction mixture was then partitioned between EtOAc (100 mL) and sat. NaCl (aq) (100 mL). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to give a brown solid residue. This residue was used in the next-step reaction without further purification: TLC (Rf =0.53; 10% MeOH/CH2Cl2).

후처리

  1. customThe reaction mixture was then partitioned between EtOAc (100 mL) and sat. NaCl (aq) (100 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a brown solid residue
  6. customThis residue was used in the next-step reaction without further purification

출처 및 근거

ORD 기록
ord-3df39bd3e3f941c2a6a496870cdbcb92
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156758

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