Trifluoroacetic acid → 5-Methylsulfanylmethyl-pyrazin-2-ylamine

HRID 719920ノート

反応式

HRID 719920 の反応式
C([O:5]C(=O)[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14][S:15][CH3:16])=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH-:5].[NH4+:7].[CH3:16][S:15][CH2:14][C:11]1[N:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=1

参加物

5

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 67482522(5-Methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester

生成物 2

HCID 14923Ammonium Hydroxide収率 0.1%HCID 218973395-Methylsulfanylmethyl-pyrazin-2-ylamine収率 201.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

A solution of (5-methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (0.45 g, 1.762 mmol) in methylene chloride (18 mL) was treated with trifluoroacetic acid (1.4 mL, 18.172 mmol) and then was stirred at 25° C. for 2 h 15 min. The reaction solution was then treated with a second aliquot of trifluoroacetic acid (0.7 mL, 9.086 mmol) and was stirred at 25° C. for 5 h. At this time, the reaction mixture was concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 1/9 methanol/methylene chloride with 0.1% ammonium hydroxide) afforded 5-methylsulfanylmethyl-pyrazin-2-ylamine (276.1 mg, quant.) as a white solid: mp 102.0–102.7° C.; EI-HRMS m/e calcd for C6H9N3S (M+) 155.0517, found 155.0516.

後処理

  1. stirringwas stirred at 25° C. for 5 h
  2. concentrationAt this time, the reaction mixture was concentrated in vacuo

出典と根拠

ORDレコード
ord-4e9e437dc3bf4b389f8d3d4843900b0f
出典データセット
uspto-grants-2006_11
特許番号
US07132425B2

反応ノート

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