2-(Di-tert-butylphosphino)biphenyl → N-methyl-N-{4-[(5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}urea

HRID 2374906Notes

Reaction equation

HRID 2374906 reaction equation
Cl.[CH3:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]2[C:11]=1[CH:10]=[N:9][C:8]([NH2:12])=[N:7]2.Br[C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:30])[C:27]([NH2:29])=[O:28])=[CH:22][CH:21]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:30][N:26]([C:23]1[CH:24]=[CH:25][C:20]([NH:12][C:8]2[N:9]=[CH:10][C:11]3=[C:3]([CH3:2])[N:4]=[C:5]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:6]3[N:7]=2)=[CH:21][CH:22]=1)[C:27]([NH2:29])=[O:28]

Participants

7

Reactant 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 57260299N-(4-bromophenyl)-N-methylureaHCID 688705435-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine hydrochloride

Product 1

HCID 68868122N-methyl-N-{4-[(5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}ureaYield 38%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

A solution of 5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine hydrochloride (26 mg, 0.1 mmol), N-(4-bromophenyl)-N-methylurea (27 mg, 0.12 mmol), tris(dibenzylideneacetone)dipalladium (10 mg, 0.01 mmol), 2-(di-t-butylphosphino)biphenyl (10 mg, 0.03 mmol) and sodium t-butoxide (25 mg, 0.23 mmol) in dioxane (0.80 mL) was added to a Smithcreator microwave reaction vessal. The vessal was sealed, then heated in the Smithcreator microwave at 160° C. for 20 minutes. After cooling to room temperature, the mixture was purified by silica gel chromatography, eluting with 5% MeOH/DCM to give N-methyl-N-{4-[(5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}urea (14 mg, 38%) as a yellow solid. 1H NMR (DMSO-d6): δ9.59 (s, 1H), 9.20 (s, 1H), 8.39-8.46 (m, 3H), 7.34-7.71 (m, 8H), 5.94 (d, J=4.67 Hz, 1H), 2.63 (d, J=4.53 Hz, 3H), 2.52 (s, 3H). MS m/z 373 (M+1).

Workup

  1. customThe vessal was sealed
  2. temperatureAfter cooling to room temperature
  3. customthe mixture was purified by silica gel chromatography
  4. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-708cd6460634424db2741b97f44e59ff
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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