Hydrochloric Acid → 1-(6-Chloro-pyrido[2,3-b]pyrazin-3-yl)-3-ethyl-thiourea

HRID 220133

反応式

HRID 220133 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:12]=1)=[N:7][C:8]([NH2:11])=[CH:9][N:10]=2.[H-].[Na+].[CH2:15]([N:17]=[C:18]=[S:19])[CH3:16].Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:12]=1)=[N:7][C:8]([NH:11][C:18]([NH:17][CH2:15][CH3:16])=[S:19])=[CH:9][N:10]=2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10966Ethyl isothiocyanateHCID 24758Sodium hydrideHCID 866355376-Chloro-pyrido[2,3-b]pyrazin-3-ylamine

生成物 1

HCID 579466641-(6-Chloro-pyrido[2,3-b]pyrazin-3-yl)-3-ethyl-thiourea収率 48.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A total of 5.0 g 6-Chloro-pyrido[2,3-b]pyrazin-3-ylamine (27.7 mmol; 1 eq) was dissolved in 150 mL of dry DMF. 1.32 g NaH (60% dispersion in mineral oil; 33.2 mmol; 1.2 eq) was added and the dark brown solution was stirred at room temperature for 1 hour. 2.4 g (27.7 mmol; 1 eq) ethyl isothiocyanate was then added and the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was then poured into 500 mL of water. The solution was neutralized with 1 N HCl whereas the product crystallizes. The brown solid was filtered of and recrystallised from dichloromethane/diethyl ether to afford 3.6 g (48.5% yield) of 1-(6-Chloro-pyrido[2,3-b]pyrazin-3-yl)-3-ethyl-thiourea.

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 3 h
  2. customcrystallizes
  3. filtrationThe brown solid was filtered of and
  4. customrecrystallised from dichloromethane/diethyl ether

出典と根拠

ORDレコード
ord-61673b71bd094f6d88ce01f1e0e12ffb
出典データセット
uspto-grants-2012_06
特許番号
US08202883B2

関連ノート

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