Dimethylformamide → HCID 118023850, compound

HRID 2171808Notes

Reaction equation

HRID 2171808 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.CN(C=O)C.CS(O[CH2:19][C:20]1[C:21]2[CH:29]=[C:28]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[S:27][C:22]=2[N:23]=[C:24]([CH3:26])[N:25]=1)(=O)=O>O>[CH:30]1([C:28]2[S:27][C:22]3[N:23]=[C:24]([CH3:26])[N:25]=[C:20]([CH2:19][N:1]4[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]4)[C:21]=3[CH:29]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6484228Thiomorpholine 1,1-dioxideHCID 118023431HCID 118023431, compound

Product 1

HCID 118023850HCID 118023850, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of thiomorpholine-1,1-dioxide (65 mg) and DMF (4 mL) were added (6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl methanesulfonate (110 mg) and TEA (150 μL), followed by stirring at room temperature for 24 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure. The residue was purified by basic silica gel column (hexane/EtOAc) to obtain 6-cyclohexyl-4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-2-methylthieno[2,3-d]pyrimidine (94 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-bfad241fc9184008becc48573f44cdd8
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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