Sodium Thiosulfate → 2-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carbaldehyde

HRID 2171792Notes

Reaction equation

HRID 2171792 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.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[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]([CH:17]=[O:18])[C:15]=3[N:16]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 118023489HCID 118023489, compound

Product 1

HCID 1180239142-(4,4-Dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine-7-carbaldehydeYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (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 DCM
  3. washThe organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09369bbf1cf94dfda322d24e9a0485bd
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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