Sodium Hydroxide → YM-976

HRID 368984Notes

Reaction equation

HRID 368984 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[C:12]([C:14]1[C:15]([NH:22][CH2:23][CH3:24])=[N:16][C:17]([CH2:20][CH3:21])=[CH:18][CH:19]=1)=O.C(=O)(O)[O-].[Na+].[OH-].[Na+]>O.O1CCCC1>[Cl:8][C:9]1[CH:10]=[C:11]([C:12]2[C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[N:16][C:15]=3[N:22]([CH2:23][CH3:24])[C:6](=[O:7])[N:5]=2)[CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 154805223-(3-Chlorobenzoyl)-6-ethyl-2-ethylaminopyridine

Product 1

HCID 6604918YM-976Yield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Chlorosulfonyl isocyanate (0.8 ml, 9 mmol) was added to a tetrahydrofuran (50 ml) solution of 3-(3-chlorobenzoyl)-6-ethyl-2-ethylaminopyridine (2.6 g, 9 mmol) under ice-cooling, followed by stirring for 1 hour under ice-cooling. To the reaction solution were added water and saturated sodium bicarbonate aqueous solution in that order, followed by 30 minutes of stirring at room temperature. This was adjusted to pH 10 with 1 N sodium hydroxide aqueous solution and extracted with chloroform. After drying the organic layer over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and the resulting filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 4-(3-chlorophenyl)-1,7-diethylpyrido[2,3-d]pyrimidin-2(1H)-one (1.7 g, 60%) in the form of crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitfollowed by 30 minutes
  4. stirringof stirring at room temperature
  5. extractionextracted with chloroform
  6. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate, magnesium sulfate
  7. customwas removed by filtration
  8. concentrationthe resulting filtrate was concentrated under a reduced pressure
  9. customThereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-3bfa86e9a0b746e7ae1c7e4a4f96996c
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

Loading…