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

HRID 1045745노트

반응식

HRID 1045745 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-301547f3284445478baddb8395d08e18
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569300B2

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