Thiomorpholine → HCID 57839070, compound

HRID 732961Notes

Reaction equation

HRID 732961 reaction equation
C(S([C:11]1[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[C:14]([C:25]([O:27][CH3:28])=[O:26])=[C:13]([CH3:29])[N:12]=1)(=O)=O)C1C=CC=CC=1.[NH:30]1[CH2:35][CH2:34][S:33][CH2:32][CH2:31]1>O1CCOCC1>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[C:15]1[C:14]([C:25]([O:27][CH3:28])=[O:26])=[C:13]([CH3:29])[N:12]=[C:11]([N:30]2[CH2:35][CH2:34][S:33][CH2:32][CH2:31]2)[N:16]=1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 57839059HCID 57839059, compound

Product 1

HCID 57839070HCID 57839070, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 2-(benzylsulfonyl)-4-(2,4-dichlorophenyl)-6-methylpyrimidine-5-carboxylate (17 mg, 0.037 mmol) in dioxane (2 mL) was added thiomorpholine (4.5 mL, 0.045 mmol). After at 40° C. for 1 hr, the reaction was concentrated under reduced pressure and diluted with EtOAc (10 mL). The organic layer was extracted with saturated NaHCO3 solution (2×6 mL), brine (5 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give methyl 4-(2,4-dichlorophenyl)-6-methyl-2-thiomorpholinopyrimidine-5-carboxylate (15 mg, 100%). The crude reaction product (>98% purity) was moved onto next step without further purification.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc (10 mL)
  3. extractionThe organic layer was extracted with saturated NaHCO3 solution (2×6 mL), brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b71d6555c1474e0ab24c1a74475e59f9
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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