Lawesson's reagent → HCID 18365062, compound

HRID 380395Notes

Reaction equation

HRID 380395 reaction equation
O=[C:2]1[NH:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)[NH:5][C:4]2[N:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>O1CCOCC1>[S:31]=[C:2]1[NH:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)[NH:5][C:4]2[N:18]=[CH:19][CH:20]=[CH:21][C:3]1=2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 18365072HCID 18365072, compound

Product 1

HCID 18365062HCID 18365062, compoundYield 152.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 3′,4′-dihydro-4′-oxospiro[piperidine-4,2′-[1′H]-(pyrido[2,3-d]-pyrimidine)]-1-carboxylate (0.74 g, 2.55 mmol) and Lawesson's reagent (0.62 g, 1.5 mmol) in dioxane (15 ml) was heated at reflux for 2 h. The mixture was absorbed onto silica gel and purified by flash column chromatography on silica gel, eluting with dichloromethane/methanol (50:1) to afford the product as a white solid (0.7 g). MS (+CI) m/Z 307 [M+H]+; 1H NMR (d6-DMSO) 10.37 (1H, dd), 8.34 (1H, dd), 8.24 (1H, dd), 8.10 (H, s), 6.76 (1H, dd), 4.04 (2H, q), 3.6-3.78 (2H, m), 3.3-3.5 (2H, m), 1.75-1.90 (4H, m), 1.21 (3H, t).

Workup

  1. temperatureat reflux for 2 h
  2. customThe mixture was absorbed onto silica gel
  3. custompurified by flash column chromatography on silica gel
  4. washeluting with dichloromethane/methanol (50:1)

Sources & evidence

ORD record
ord-1232e07e0f3a4a2a84b3e846caee62be
Source dataset
uspto-grants-2001_10
Patent number
US06303613B1

Reaction notes

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