Phosphorus sulfide (P2S5) → HCID 118599135, compound

HRID 1050361Notes

Reaction equation

HRID 1050361 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[C:5](=O)[NH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[C:5](=[S:22])[NH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)2×HCID 118598746HCID 118598746, compound

Product 1

HCID 118599135HCID 118599135, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A vial was charged with 3-chloro-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridine-2-carboxylate (3, 0.35, 1.2 mmol) and pyridine (10 mL) was added. To the above mixture phosphorus pentasulfide (0.53 g, 2.4 mmol) was added and reaction was heated at 110° C. for 16 h. TLC showed presence of starting material and phosphorus pentasulfide (0.265 g, 1.2 mmol) was added again and heated the reaction to 115° C. for 24 h. The pyridine was removed under reduced pressure and water (20 mL) was added and extracted with 5% methanol in dichloromethane (100 mL). The organic layer was washed with sodium bicarbonate and brine and layer was concentrated to dryness to afford ethyl 3-chloro-5-(pyrimidin-4-ylamino)-6-thioxo-1,6-dihydropyridine-2-carboxylate (4) as brownish yellow solid and used directly without further purification. Yield: 350 mg, crude; MS (ESI) m/z 310.94 [M+1]+.

Workup

  1. additionwas added
  2. customreaction
  3. additionwas added again
  4. temperatureheated
  5. customthe reaction to 115° C. for 24 h
  6. customThe pyridine was removed under reduced pressure and water (20 mL)
  7. additionwas added
  8. extractionextracted with 5% methanol in dichloromethane (100 mL)
  9. washThe organic layer was washed with sodium bicarbonate and brine and layer
  10. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-e611304eb8d7473288991538abab1235
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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