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

HRID 1045745Notes

Reaction equation

[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

Participants

Conditions

Temperature: 120 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-301547f3284445478baddb8395d08e18
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569300B2

Reaction notes

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