1,4-Dioxane → 6-(Methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 928232Notes

Reaction equation

HRID 928232 reaction equation
Br[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:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:12][S:11][C:7]1[N:6]=[C:5]2[NH:4][N:3]=[C:2]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]2=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 178503373HCID 178503373, compoundHCID 178527066HCID 178527066, compound

Product 1

HCID 1785033766-(Methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidineYield 87.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

A microwave tube was charged with 3-bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (1.0 g, 4.0 mmol), phenylboronic acid (1.5 g, 12 mmol), potassium phosphonate (2.5 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0.35 g, 0.30 mmol), dioxane (16 mL) and water (4 mL). The mixture was heated in microwave at 150° C. for 20 min. The reaction mixture was poured into water. The aqueous layer was extracted with EtOAc (10×). The combined organic layer was dried (Na2SO4), concentrated, and purified to provide 6-(methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine (0.85 g, 87%) as a white solid. MS m/z 243.1 [M+H]+.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (10×)
  2. dry with materialThe combined organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-fa2e1526cd40497990c1910231234df8
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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