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

HRID 1274145

反応式

HRID 1274145 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3df39bd3e3f941c2a6a496870cdbcb92
出典データセット
uspto-grants-2000_12
特許番号
US06156758

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