Methanesulfonyl chloride → [2-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methyl methanesulfonate

HRID 2171782Notes

Reaction equation

HRID 2171782 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][CH:5]([C:8]2[S:9][C:10]3[N:11]=[C:12]([CH3:19])[N:13]=[C:14]([CH2:17][OH:18])[C:15]=3[N:16]=2)[CH2:4][CH2:3]1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>CCOC(C)=O>[CH3:21][S:22]([O:18][CH2:17][C:14]1[C:15]2[N:16]=[C:8]([CH:5]3[CH2:4][CH2:3][C:2]([CH3:20])([CH3:1])[CH2:7][CH2:6]3)[S:9][C:10]=2[N:11]=[C:12]([CH3:19])[N:13]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 118023489HCID 118023489, compound

Product 1

HCID 118023977[2-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methanol (6.42 g) and EtOAc (65 mL) were added dropwise TEA (4.5 mL) and MsCl (2.1 mL) under ice-cooling, followed by stirring at 0° C. for 1 hour. The reaction mixture was filtered and then to the liquid was added saturated aqueous sodium bicarbonate, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure to obtain [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methyl methanesulfonate (9.3 g).

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered
  3. additionto the liquid was added saturated aqueous sodium bicarbonate
  4. extractionfollowed by extraction with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-906161eebe484381a6d936a629ee837c
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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