2-(4-Methylphenyl)-9-phenylethynyl-2,6-dihydro[1,2,4]triazolo[4,3-c]-quinazoline-3,5-dione → 2-(4-Methylphenyl)-9-(2-phenylethyl)-2,6-dihydro[1,2,4]-triazolo[4,3-c]-quinazoline-3,5-dione

HRID 2406207Notes

Reaction equation

HRID 2406207 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:29](=[O:30])[N:11]3[C:12](=[O:28])[NH:13][C:14]4[CH:15]=[CH:16][C:17]([C:20]#[C:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1>ClCCl.CO.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:29](=[O:30])[N:11]3[C:12](=[O:28])[NH:13][C:14]4[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 1361415722-(4-Methylphenyl)-9-phenylethynyl-2,6-dihydro[1,2,4]triazolo[4,3-c]-quinazoline-3,5-dione

Product 1

HCID 1358703222-(4-Methylphenyl)-9-(2-phenylethyl)-2,6-dihydro[1,2,4]-triazolo[4,3-c]-quinazoline-3,5-dioneYield 79.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A catalytic amount of 10% Pd/C and 13a (20.0 mg, 0.0510 mmol) in a mixture of 2 mL of dichloromethane and 2 mL of methyl alcohol was stirred during 12 h under H2 at atmospheric pressure. The mixture was filtered through celite, washed with additionally methyl alcohol and triturated from ethyl alcohol to afford 14a (16 mg, 0.0404 mmol, 79%) as a white solid. mp: 303° C.;

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with additionally methyl alcohol
  3. customtriturated from ethyl alcohol

Sources & evidence

ORD record
ord-53b4a3c2c3d14803bfc791abef94e684
Source dataset
uspto-grants-2014_08
Patent number
US08809355B2

Reaction notes

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