Sodium Carbonate → HCID 18507239, compound

HRID 1356097Notes

Reaction equation

HRID 1356097 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Br)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=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]>[NH2:1][C:2]1[N:3]=[C:4]([S:11][CH3:12])[C:5]([C:9]#[N:10])=[C:6]([C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 18507239HCID 18507239, compoundYield 20%

Reagents, catalysts & solvents 2

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

Procedure

To a stirred suspension of 2,45 g (10.0 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 65 ml dioxane at room temperature were added 2.18 g (20.0 mmol) 3-pyridineboronic acid, 1.15 g (1.00 mmol) tetrakis(triphenylphosphine)palladium(O) and 20 ml (40.0 mmol) 2M aqueous sodium carbonate. The reaction mixture was heated at reflux for 48 h, then concentrated in vacuo. Chromatography (1/4 ethyl acetate/hexane) afforded 460 mg (20%) 2-amino-4-methylsulfanyl-6-pyridin-3-yl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 243 (M+, 100), 242 ([M—H]+, 70).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d77262ea479a4b258886ce47328cc6a9
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…