Boron tribromide → HCID 136360264, compound

HRID 1270324Notes

Reaction equation

HRID 1270324 reaction equation
[CH2:1]([C:3]1[C:4]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[N:5][C:6]([CH2:19][CH3:20])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][C:10]=2[O:17]C)[N:8]=1)[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([C:3]1[C:4]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[N:5][C:6]([CH2:19][CH3:20])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=2[OH:17])[N:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18449319HCID 18449319, compound

Product 1

HCID 136360264HCID 136360264, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 23) in dichloromethane was added BBr3 (1N,6 ml)at −78° C. The mixture is stirred for 10 min then gradually warmed to room temperature and stirred for 3 hr before being poured into ice-water and extracted with dichloromethane. The aqueous layer was basified with sat. NaHCO3 and extracted with dichloromethane. The combined extracts were dried (sodium sulfate), filtered, concentrated and the residue is purified by column (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 (t, 1H), 6.51 (d, 1H), 7.27 (d, 1H). LC-MS: 330 (M+1).

Workup

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

Sources & evidence

ORD record
ord-e6a90d30689a43a19e5538e39af6c226
Source dataset
uspto-grants-2007_04
Patent number
US07202250B2

Reaction notes

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