Cesium carbonate → HCID 18507295, compound

HRID 1356018Notes

Reaction equation

HRID 1356018 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.C([Sn](CCCC)(CCCC)[C:21]([O:23][CH2:24][CH3:25])=[CH2:22])CCC.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:24]([O:23][C:21]([C:11]1[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:7][C:8]([NH2:15])=[N:9][C:10]=1[S:13][CH3:14])=[CH2:22])[CH3:25]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 185075894-Furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine

Product 1

HCID 18507295HCID 18507295, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1.12 g (3.37 mmol) 4-furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine in 30 ml dioxane under argon at room temperature were added 1.25 ml (3.70 mmol) tributyl(I-ethoxyvinyl)tin, 236 mg (0.34 mmol) bis(triphenylphosphine) palladium(II) chloride and 2.19 g (6.74 mmol) cesium carbonate. 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 (1/2 ethyl acetate/hexane) afforded 730 mg (78%) 5-(1-ethoxy-vinyl)-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine as an orange crystalline solid. ES-MS m/e (%): 278 (M+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-1371f601de25488daf36d3d7f79f2a09
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…