4-Hydroxybenzylamine → 4-{[(3-Amino-6-bromopyrazin-2-yl)amino]methyl}phenol

HRID 1297322Notes

Reaction equation

HRID 1297322 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1>CS(C)=O>[NH2:9][C:3]1[C:2]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:7][C:6]([Br:8])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 974724-HydroxybenzylamineHCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 248204284-{[(3-Amino-6-bromopyrazin-2-yl)amino]methyl}phenolYield 11.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3,5-dibromo-pyrazin-2-ylamine (220 mg, 0.87 mmol) and 4-aminomethyl-phenol (225.0 mg, 1.83 mmol) in DMSO (2.5 mL) was heated at 98° C. under nitrogen for 24 hours. HPLC showed that 35% of product was formed and 40% of starting material presented. The reaction solution was partitioned between EtOAc and water. After condensation of organic layer, the residue was purified on a silica gel column eluting with 3% methanol in dichloromethane to provide 4-[(3-amino-6-bromo-pyrazin-2-ylamino)-methyl]-phenol (30 mg) as a yellow solid.

Workup

  1. customwas formed
  2. customThe reaction solution was partitioned between EtOAc and water
  3. customAfter condensation of organic layer
  4. customthe residue was purified on a silica gel column
  5. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-f54413153dba4639ab1ace9cd9bb69ca
Source dataset
uspto-grants-2007_07
Patent number
US07250417B2

Reaction notes

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