Dimethyl Sulfoxide → tert-butyl 4-((3-bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate

HRID 928228Notes

Reaction equation

HRID 928228 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([S:11][CH3:12])=[N:8][CH:9]=2)[NH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].CS(C)=O.Br[CH2:24][CH:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:32](=[O:34])[O-:33])[CH2:27][CH2:26]1>O.C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([S:11][CH3:12])=[N:8][CH:9]=2)[N:4]([CH2:24][CH:25]2[CH2:30][CH2:29][CH:28]([NH:31][C:32](=[O:34])[O:33][C:10]([CH3:2])([CH3:5])[CH3:9])[CH2:27][CH2:26]2)[N:3]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 866775084-(Bromomethyl)cyclohexylcarbamateHCID 178503373HCID 178503373, compound

Product 1

HCID 67470870tert-butyl 4-((3-bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamateYield 165.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

A 10 mL microwave tube was charged with 3-bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (0.3 g, 1.22 mmol), K2CO3 (0.51 g, 3.66 mmol), and DMSO (2 mL). The mixture was stirred for 20 min before 4-(bromomethyl)cyclohexylcarbamate (0.45 g, 1.53 mmol) and THF (4 mL) was added. The resulting mixture was heated at 150° C. for 10 minutes in microwave. The reaction mixture was poured into water and extracted with Et2O (3×). The combined ether layer was dried (Na2SO4) and concentrated. The crude mixture was purified by Isco to provide tert-butyl 4-((3-bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate (0.46 g, 83%) as a white solid. MS m/z 478.10 [M+Na]+.

Workup

  1. additionwas added
  2. extractionextracted with Et2O (3×)
  3. dry with materialThe combined ether layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude mixture was purified by Isco

Sources & evidence

ORD record
ord-19760be9a0bf4565af571210422e54b7
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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