Water → HCID 57982477, compound

HRID 1868469Notes

Reaction equation

HRID 1868469 reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:8]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:7]2[CH:30]=1)(=O)[NH2:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1.O>C1COCC1>[C:1]([C:4]1[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:8]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:7]2[CH:30]=1)(=[S:40])[NH2:2]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 86606998HCID 86606998, compound

Product 1

HCID 57982477HCID 57982477, compoundYield 220.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of tert-butyl (2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (intermediate for Example 62, 150 mg, 0.33 mmol) in THF (10 mL) was added Lawesson's reagent (202 mg, 0.50 mmol). After heating to 65° C. for 20 h, the reaction mixture was poured into H2O (5 mL). The resulting mixture was extracted with EtOAc and the organic layer was washed with satd aq NH4Cl and brine prior to drying over MgSO4. Filtration, concentration under reduced pressure afforded crude tert-butyl (2-carbamothioyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (339 mg, 100% crude yield) as a yellow oil.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washthe organic layer was washed with satd aq NH4Cl and brine
  3. dry with materialto drying over MgSO4
  4. filtrationFiltration, concentration under reduced pressure

Sources & evidence

ORD record
ord-5c137824ea394bcf87b613e0105111fc
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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