Sodium Carbonate → 5-(3,5-Dichloro-phenyl)-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

HRID 1355840Notes

Reaction equation

HRID 1355840 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11](I)=[C:10]([S:13][CH3:14])[N:9]=[C:8]([NH2:15])[N:7]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[C:21]([Cl:23])[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Cl:16][C:17]1[CH:18]=[C:19]([C:11]2[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[N:7][C:8]([NH2:15])=[N:9][C:10]=2[S:13][CH3:14])[CH:20]=[C:21]([Cl:23])[CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343313,5-Dichlorophenylboronic acidHCID 185075894-Furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine

Product 1

HCID 185073895-(3,5-Dichloro-phenyl)-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamineYield 62.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 500 mg (1.50 mmol) 4-furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine in 20 ml dioxane under argon at room temperature were added 0.5 ml (1.50 mmol) 3,5-dichlorophenylboronic acid (50% solution in THF/water), 173 mg (0.15 mmol) tetrakis(triphenylphosphine)palladium(O) and 3.0 ml (6.0 mmol) 2M aqueous sodium carbonate solution. The reaction mixture was heated at reflux for 16 h, then cooled to room temperature, 1 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane) followed trituration in ether/hexane afforded 328 mg (62%) 5-(3,5-dichloro-phenyl)-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine as a beige crystalline solid. ES-MS m/e (%):354 (M{37Cl}+H+, 60), 352 (M{35Cl}+H+, 100).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. addition1 g of kieselgel added
  4. concentrationthe mixture concentrated in vacuo

Sources & evidence

ORD record
ord-e63ffaa877fb47298cfba14169539a7c
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…