Water → HCID 178503373, compound

HRID 928227Notes

Reaction equation

HRID 928227 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]2[NH:9][NH:10][C:11](=O)[C:6]2=[CH:5][N:4]=1.P(Br)(Br)([Br:15])=O.O.[OH-].[NH4+]>CC#N>[Br:15][C:11]1[C:6]2[C:7](=[N:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=2)[NH:9][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24613Phosphorus oxybromideHCID 336981046-(Methylthio)-1H-pyrazolo[3,4-D]pyrimidin-3(2H)-one

Product 1

HCID 178503373HCID 178503373, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
100 °C

Procedure

To a suspension of 6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (0.50 g, 2.7 mmol) in CH3CN (15 mL) was added a CH3CN solution of P(O)Br3 (1.57 g, 5.5 mmol) in a pressure vessel. The mixture was sonicated for 30 min before being heated to 100° C. for 16 h (overnight). After it was cooled to 0° C., H2O and aqueous ammonium hydroxide were added to basify the mixture. The mixture was stirred at 0° C. for 1 h. The aqueous layer was extracted with EtOAc (10×). The combined EtOAc layer was dried (Na2SO4), and concentrated to give 3-bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (0.51 g, 77%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.00 (s, 1H), 5.57 (s, 3H); MS m/z 245.00 [M+H]+.

Workup

  1. customThe mixture was sonicated for 30 min
  2. temperatureAfter it was cooled to 0° C.
  3. extractionThe aqueous layer was extracted with EtOAc (10×)
  4. dry with materialThe combined EtOAc layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4c7a03c914d74f78a19cbb3e18c732fd
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

Loading…