Ammonium Hydroxide → Tert-butyl 4-(3-amino-5-bromopyrazin-2-yl)piperazine-1-carboxylate

HRID 1045745ノート

反応式

HRID 1045745 の反応式
[Br:1][C:2]1[N:3]=[C:4](Cl)[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH-].[NH4+:23]>O>[NH2:23][C:4]1[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=[C:2]([Br:1])[N:3]=1

参加物

4

反応物 2

HCID 14923Ammonium HydroxideHCID 58447006Tert-butyl 4-(5-bromo-3-chloropyrazin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 58446968Tert-butyl 4-(3-amino-5-bromopyrazin-2-yl)piperazine-1-carboxylate収率 51%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A 300 mL pressure vessel was charged with tert-butyl 4-(5-bromo-3-chloropyrazin-2-yl)piperazine-1-carboxylate (5.0 g, 13 mmol) and concentrated ammonium hydroxide (60 mL). The vessel was sealed and the reaction mixture was magnetically stirred at 120° C. for 12 h. After the reaction mixture was cooled to room temperature, the vessel was opened and the resulting mixture was poured into water (100 mL) and extracted with CH2Cl2 (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 3% EtOAc in CH2Cl2 (containing 2% Et3N), to afford 2.4 g (51%) of the product as a white solid. MS m/z: 358 (M+H+).

後処理

  1. customThe vessel was sealed
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. extractionextracted with CH2Cl2 (50 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with 3% EtOAc in CH2Cl2 (containing 2% Et3N)

出典と根拠

ORDレコード
ord-301547f3284445478baddb8395d08e18
出典データセット
uspto-grants-2013_10
特許番号
US08569300B2

反応ノート

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