Dibutyltin oxide → HCID 10292839, compound

HRID 586299Notes

Reaction equation

HRID 586299 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([OH:20])([CH3:19])[CH3:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:21]1[C:26]([C:27]([NH2:29])=O)=[CH:25][N:24]=[CH:23][N:22]=1.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([OH:20])([CH3:19])[CH3:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:21]1[C:26]([C:27]#[N:29])=[CH:25][N:24]=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 61221Dibutyltin oxideHCID 57438128HCID 57438128, compound

Product 1

HCID 10292839HCID 10292839, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-{2-fluoro-5-[3-(1-hydroxy-1-methylethyl)-imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl}pyrimidine-5-carboxylic acid amide (50 mg, 0.13 mmol) was formed in dry toluene (50 ml). Dibutyltin oxide (6 mg, 0.03 mmol) was added and the mixture heated at reflux for 18 h. The solvent was removed under reduced pressure then purification by chromatography (silica gel, 3% MeOH/CH2Cl2) gave the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 1.72 (6H, s), 3.23 (1H, s), 7.45 (1H, dd, J 9, 1 Hz), 8.24-8.29 (1H, m), 8.30 (1H, s), 8.42 (1H, dd, J 7, 2 Hz), 8.81 (1H, s), 9.14 (1H, s), 9.51 (1H, s); MS (ES+) m/z 376 [M+H]+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 h
  3. customThe solvent was removed under reduced pressure
  4. custompurification by chromatography (silica gel, 3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-249dd1e319a84df8bb9dd8614f586410
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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