Boron tribromide → HCID 136360264, compound

HRID 349177Notes

Reaction equation

HRID 349177 reaction equation
B(Br)(Br)Br.[CH2:5]([C:7]1[C:8]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[N:9][C:10]([CH2:23][CH3:24])=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:14]=2[O:21]C)[N:12]=1)[CH3:6]>ClCCl>[CH2:5]([C:7]1[C:8]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[N:9][C:10]([CH2:23][CH3:24])=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[OH:21])[N:12]=1)[CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18449319HCID 18449319, compound

Product 1

HCID 136360264HCID 136360264, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 is added to a solution of 3,6-diethyl-5-(2,4-dimethoxyphenyl)-[N-(1-ethylpropyl)]pyrazine-2-amine (910 mg, 2.54 mmol). (obtained in example 4) in dichloromethane (1N, 6 ml) at −78° C. The mixture is stirred for 10 minutes, then gradually warmed to room temperature and stirred for 3 hours before being poured into ice-water and extracted with dichloromethane. The aqueous layer is basified with saturated NaHCO3 and extracted with dichloromethane. The combined extracts are dried (sodium sulfate), filtered, concentrated and the residue is purified by column chromatography (20% EtOAc in hexane) to give 3,6-diethyl-5-(2,4-dihydroxyphenyl)-[N-(1-ethylpropyl)]pyrazine-2-amine as a yellow oil (590 mg, 71%): 1H NMR (CDCl3, 400 MHz) δ 0.94 (t,6H), 1.30(t,3H), 1.36(t,3H), 1.57(m,2H), 1.67(m,2H), 2.62(q,2H), 2.86(q,2H), 4.15(m, 2H), 6.41(d,1H) 6.51(d,1H), 7.27(d,1H). LC-MS: 330 (M+1).

Workup

  1. stirringstirred for 3 hours
  2. extractionextracted with dichloromethane
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined extracts are dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue is purified by column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-9e1ec3c049cd41f18477746cfbbc916f
Source dataset
uspto-grants-2007_02
Patent number
US07179807B2

Reaction notes

Loading…