5-Hydroxyindole → 1H-Indole, 5-[[6-[(phenylmethoxy)methyl]-4-pyrimidinyl]oxy]-

HRID 453134

Reaction equation

HRID 453134 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH2:11]([O:18][CH2:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH2:11]([O:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]=[C:24]([O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH:25]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 160545-HydroxyindoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 534212594-((Benzyloxy)methyl)-6-chloropyrimidine

Product 1

HCID 593942601H-Indole, 5-[[6-[(phenylmethoxy)methyl]-4-pyrimidinyl]oxy]-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-hydroxy indole (1.33 g, 10 mmol) and 4-benzyloxymethyl-6-chloro-pyrimidine (2.35 g, 10 mmol) in acetonitrile (20 mL) is added DBU. After 16 h at rt the solution is concentrated under reduced pressure. The residue is purified by FCC (EtOAc/Heptane from 0% to 40%) to give 5-(6-benzyloxymethyl-pyrimidin-4-yloxy)-1H-indole. MS (ESI) m/z 447.0 (M+1).

Workup

  1. concentrationAfter 16 h at rt the solution is concentrated under reduced pressure
  2. customThe residue is purified by FCC (EtOAc/Heptane from 0% to 40%)

Sources & evidence

ORD record
ord-7cb274b658ab4bdb816a8f488bb21c0a
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Linked notes

Loading…