Water → HCID 178512066, compound

HRID 2242886

Reaction equation

HRID 2242886 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]#[N:16].[Al+3].[Cl-].[Cl-].[Cl-].O>ClC(Cl)C>[Br:1][C:2]1[C:3]([NH:9][C:15]([C:11]2[O:10][CH:14]=[CH:13][CH:12]=2)=[NH:16])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 692452-FuronitrileHCID 6200042-Amino-3,5-dibromopyrazineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178512066HCID 178512066, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3,5-dibromo-pyrazin-2-ylamine (608 mg, 2.4 mmol), furan-2-carbonitrile (297 uL, 3.39 mmol) and AlCl3 (320 mg, 2.4 mmol) in dichloroethane (6 ml) was heated at 115° C. overnight. The reaction was cooled to room temperature and water (5 ml) was added. After 30 minutes, the resulting precipitate was collected and purified by column chromatography (SiO2, THF) to afford 595 mg (72%) of N-(3,5-dibromo-pyrazin-2-yl)-furan-2-carboxamidine as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 6.73 (dd, J=3.4, 1.8 Hz, 1H), 7.3 (dd, J=3.1 Hz, 1H), 7.98 (s, 1H), 8.49(s, 1H), 8.69 (br. s, 1H).

Workup

  1. customthe resulting precipitate was collected
  2. custompurified by column chromatography (SiO2, THF)

Sources & evidence

ORD record
ord-e652283c74b74d7c9aa07581e79364ed
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Linked notes

Loading…