Lawesson's reagent → 4,6-Dimethoxy-pyrimidin-2-carbothioic acid amide

HRID 388708Notes

Reaction equation

HRID 388708 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([NH2:13])=O)[N:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11](=[S:23])[NH2:13])[N:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 582826824,6-Dimethoxypyrimidin-2-carboxylic acid amide

Product 1

HCID 582827014,6-Dimethoxy-pyrimidin-2-carbothioic acid amideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of compound 286 (21.86 g, 1 eq.) in dry THF (200 mL) was added Lawesson's reagent (29 g, 0.6 eq.) under nitrogen. The mixture was then stirred at 90° C. for 1 hr and then concentrated in vacuo. The residue obtained was triturated in a DCM/diisopropyl ether mixture to yield compound 287 as an orange solid in 72% yield. MS (ESI, EI+): m/z=200 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. customwas triturated in a DCM/diisopropyl ether mixture

Sources & evidence

ORD record
ord-5c6f87f7e9d8444c94eb1985514bd866
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

Loading…