3-Aminostyrene → (E)-5-(3-aminostyryl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine

HRID 2284718Notes

Reaction equation

HRID 2284718 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])=[CH2:2].[F:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]2[N:23]=[C:22]([NH:24][CH2:25][CH2:26][CH3:27])[C:21](I)=[CH:20][N:19]=2)[CH:14]=[CH:15][CH:16]=1>C(#N)C.C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:6][C:5]1[CH:4]=[C:3]([CH:9]=[CH:8][CH:7]=1)/[CH:1]=[CH:2]/[C:21]1[C:22]([NH:24][CH2:25][CH2:26][CH3:27])=[N:23][C:18]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([F:10])[CH:12]=2)=[N:19][CH:20]=1

Participants

6

Reactant 2

HCID 42600413-AminostyreneHCID 90051756HCID 90051756, compound

Product 1

HCID 90051755(E)-5-(3-aminostyryl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-vinylaniline (19 μL), N2-(3-fluorophenyl)-5-iodo-N4-propylpyrimidine-2,4-diamine (F2, 51 mg) and palladium(II) acetate (3 mg) in acetonitrile (1.5 mL), triethylamine (68 μL) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour, and then stirred at 80° C. for 14 hours. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 50% hexane in ethyl acetate) to obtain (E)-5-(3-aminostyryl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine (F11, 14 mg).

Workup

  1. stirringstirred at 80° C. for 14 hours
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (eluent, 50% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-b026facf729341869ed912bb4000df84
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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