2-Methyl-2-butene → 2-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carboxylic acid

HRID 2171793Notes

Reaction equation

HRID 2171793 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]([CH:17]=[O:18])[C:15]=3[N:16]=2)[CH2:4][CH2:3]1.CC(=CC)C.[O-:26]Cl=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CC(C)=O.O>[CH3:1][C:2]1([CH3:20])[CH2:3][CH2:4][CH:5]([C:8]2[S:9][C:10]3[N:11]=[C:12]([CH3:19])[N:13]=[C:14]([C:17]([OH:26])=[O:18])[C:15]=3[N:16]=2)[CH2:6][CH2:7]1

Participants

8

Reactant 5

HCID 105532-Methyl-2-buteneHCID 24436Sodium SulfateHCID 24477Sodium ThiosulfateHCID 23668197Sodium ChloriteHCID 1180239142-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carbaldehyde

Product 1

HCID 1180240312-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a mixture of [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methanol (500 mg) and DCM (10 mL) was added Dess-Martin periodinane (1.46 g) under ice-cooling, followed by stirring at 0° C. for 3 hours. To the reaction mixture was added an aqueous Na2S2O3 solution, followed by extraction with DCM. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over Na2SO4, and then concentrated under reduced pressure to obtain 2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carbaldehyde (492 mg). To a mixture of the obtained aldehyde, NaH2PO4 (245 mg), 2-methyl-2-butene (542 μL), water (5 mL), and acetone (10 mL) was added NaClO2 (231 mg) under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture were added an aqueous Na2S2O3 solution and Na2SO4, followed by extraction with a mixed solution (1:9) of 2-propanol and chloroform. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure to obtain 2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carboxylic acid (870 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with a mixed solution (1:9) of 2-propanol and chloroform
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b2dc470b0ca4398b0acfe49c2b36a50
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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