1-Butanol → HCID 72191063, compound

HRID 388084Notes

Reaction equation

HRID 388084 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:5]([NH2:17])=[N:4][CH:3]=1.C[C@@H](N)C1C=CC=CC=1.NC1C(Br)=NC(Br)=CN=1.CCC[CH2:39][OH:40]>>[C:11]1([C@H:9]([N:8]2[C:6]3=[N:7][CH:2]=[CH:3][N:4]=[C:5]3[NH:17][C:39]2=[O:40])[CH3:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Br:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])[C:5]([NH2:17])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 6200042-Amino-3,5-dibromopyrazineHCID 6431891-Phenethylamine, (+)-HCID 72191063HCID 72191063, compound

Product 2

HCID 66699735HCID 66699735, compoundHCID 72191063HCID 72191063, compoundYield 55%

Procedure

(R)-6-Bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine. The title compound was prepared using (R)-α-methylbenzylamine (2.28 mL, 17.93 mmol), 2-amino-3,5-dibromo-pyrazine (3.00 g, 11.96 mmol), and n-BuOH (30 mL) as described in General Procedure A. The crude compound was purified via silica gel chromatography (20%-30% EtOAc in hexanes). Clean fractions were combined and condensed, and subsequently triturated from methanol with water while sonicating to afford 1.92 g (6.54 mmol, 55%) of (R)-6-bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine. MS (ESI) m/z 294.0 [M+1]+.

Workup

  1. customThe crude compound was purified via silica gel chromatography (20%-30% EtOAc in hexanes)
  2. customcondensed
  3. customsubsequently triturated from methanol with water
  4. customwhile sonicating

Sources & evidence

ORD record
ord-50f07cda0fc7414fa03e311494f332c4
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

Loading…