Phosphorus sulfide (P2S5) → HCID 15461577, compound

HRID 368991Notes

Reaction equation

HRID 368991 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[Cl:15][C:16]1[CH:17]=[C:18]([C:22]2[C:23]3[CH:33]=[CH:32][C:31]([CH3:34])=[N:30][C:24]=3[N:25]([CH2:28][CH3:29])[CH2:26][N:27]=2)[CH:19]=[CH:20][CH:21]=1.C(=O)(O)[O-].[Na+]>ClCCCl>[Cl:15][C:16]1[CH:17]=[C:18]([C:22]2[C:23]3[CH:33]=[CH:32][C:31]([CH3:34])=[N:30][C:24]=3[N:25]([CH2:28][CH3:29])[C:26](=[S:2])[N:27]=2)[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 23284529HCID 23284529, compound

Product 1

HCID 15461577HCID 15461577, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Diphosphorus pentasulfide (3.00 g, 13.5 mmol) was added to a solution of 2.00 g (6.69 mmol) of 4-(3-chlorophenyl)-1-ethyl-7-methylpyrido[2,3-d]pyrimidine in 100 ml of 1,2-dichloroethane, followed by heating under reflux for 6 hours. The reaction solution was cooled to room temperature, mixed with saturated sodium bicarbonate and extracted with chloroform. The organic layer was washed with brine and dried 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-chloroform) and further recrystallized from ethyl acetate-diisopropyl ether to give 1.14 g of 4-(3-chlorophenyl)-1-ethyl-7-methylpyrido[2,3-d]pyrimidin-2(1H)-thione. The yield was 54%.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate, magnesium sulfate
  6. customwas removed by filtration
  7. concentrationthe resulting filtrate was concentrated under a reduced pressure
  8. customThereafter, the resulting residue was purified by silica gel column chromatography (hexane-chloroform)
  9. customfurther recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-5bd02f03a7994b9d856975885bc0fee7
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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