Thiomorpholine → HCID 57982502, compound

HRID 1868452Notes

Reaction equation

HRID 1868452 reaction equation
Br[C:2]1[N:23]=[C:5]2[N:6]=[C:7]([CH3:22])[C:8]([C:18]([O:20][CH3:21])=[O:19])=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])[N:4]2[N:3]=1.[NH:24]1[CH2:29][CH2:28][S:27][CH2:26][CH2:25]1>O1CCOCC1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[C:9]1[N:4]2[N:3]=[C:2]([N:24]3[CH2:29][CH2:28][S:27][CH2:26][CH2:25]3)[N:23]=[C:5]2[N:6]=[C:7]([CH3:22])[C:8]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 57982522HCID 57982522, compound

Product 1

HCID 57982502HCID 57982502, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of methyl 2-bromo-7-(2,4-dichlorophenyl)-5-methyl-[1,2,4]-triazolo[1,5-a]pyrimidine-6-carboxylate (30 mg, 0.07 mmol) in dioxane (2 mL) was added thiomorpholine (15 μL, 0.14 mmol). After heating to 75° C. for 16 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with satd aq NH4Cl and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded methyl 7-(2,4-dichlorophenyl)-5-methyl-2-thiomorpholino-[1,2,4]-triazolo[1,5-a]pyrimidine-6-carboxylate (28 mg, 90%) as a yellow solid.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with satd aq NH4Cl and brine
  4. dry with materialto drying over anhydrous MgSO4
  5. filtrationFiltration, concentration
  6. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-73ff50dd2fb9452b85812dabdecb2fb5
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

Loading…