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

HRID 3173

Reaction equation

HRID 3173 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-9cc63b0f6a514bce8d35b9f03404b410
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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