Methanesulfonyl chloride → [6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate

HRID 2171781Notes

Reaction equation

HRID 2171781 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][CH:5]([C:8]2[S:19][C:11]3[N:12]=[C:13]([CH3:18])[N:14]=[C:15]([CH2:16][OH:17])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:21][S:22]([O:17][CH2:16][C:15]1[C:10]2[CH:9]=[C:8]([CH:5]3[CH2:6][CH2:7][C:2]([CH3:20])([CH3:1])[CH2:3][CH2:4]3)[S:19][C:11]=2[N:12]=[C:13]([CH3:18])[N:14]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 118023561(6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl)methanol

Product 1

HCID 118023751[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methanol (16.0 g), TEA (10 mL) and DCM (200 mL) was added dropwise MsCl (5.0 mL) at 0° C. for 15 minutes, followed by stirring at the same temperature for 1 hour. To the reaction mixture was added saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine. To the organic layer were added MgSO4, activated carbon (5 g), and basic silica gel (20 mL), followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure to obtain [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate (18.9 g).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine
  3. additionTo the organic layer were added MgSO4, activated carbon (5 g), and basic silica gel (20 mL)
  4. stirringby stirring
  5. filtrationThe mixture was filtered through Celite
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3405115bdfe44cb08d89c329a32181d1
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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