Lawesson's reagent → HCID 86678219, compound

HRID 2362297Notes

Reaction equation

HRID 2362297 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@@H:6]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[NH:7][C:8](=O)[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:10]=1[CH3:11])=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C@@H:6]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[NH:7][C:8](=[S:40])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:10]=1[CH3:11])=[O:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 71293479HCID 71293479, compound

Product 1

HCID 86678219HCID 86678219, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (R)-4-(4-cyano-phenyl)-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester (14.5 g, 35 mmol) (prepared according to WO 2006/082412, which is incorporated herein by reference in its entirety) in toluene (105 mL) under an atmosphere of N2, was added Lawesson's reagent (17 g, 42 mmol), and the resulting mixture stirred at 120° C. for 17 hours. The reaction mixture was allowed to cool to RT and then evaporated in vacuo. The resulting residue was dissolved in diethyl ether, filtered, and the filtrate collected, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 10-40% EtOAc in cyclohexane to yield the title compound as a yellow foam (4.8 g).

Workup

  1. temperatureto cool to RT
  2. customevaporated in vacuo
  3. dissolutionThe resulting residue was dissolved in diethyl ether
  4. filtrationfiltered
  5. customthe filtrate collected
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with a gradient of 10-40% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-dd234bb48bda474f88cfecfd9b017f81
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

Loading…