Lawesson's reagent → 2-Amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]-pyrimidin-7(8H)-thion

HRID 53632Notes

Reaction equation

HRID 53632 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9](=O)[N:8]([CH3:21])[C:6]=2[N:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>N1C=CC=CC=1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9](=[S:31])[N:8]([CH3:21])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 53278642-amino-6-(2,6-dichlorophenyl)-8-methyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 116529512-Amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]-pyrimidin-7(8H)-thion

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.321 g (1.0 mmol) of 2-amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]pyrimidin-7-(8H)-one from Example 12 and 0.404 g (1.0 mmol) of Lawesson's Reagent in 10 mL of pyridine was heated at reflux with stirring for 24 hours. The solvent was evaporated under reduced pressure, and the residue was triturated with 20 mL of water, filtered, and the cake washed well with water. Purification was by silica gel chromatography to afford the desired compound identified as 2-amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]-pyrimidin-7(8H)-thione.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was triturated with 20 mL of water
  5. filtrationfiltered
  6. washthe cake washed well with water
  7. customPurification

Sources & evidence

ORD record
ord-467770a90aae44328007c933558082d1
Source dataset
uspto-grants-1997_04
Patent number
US05620981

Reaction notes

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