Water → 3-bromo-1-methyl-6-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1351148Notes

Reaction equation

HRID 1351148 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=[C:5]2[C:4](=O)[NH:3]1.P(Br)(Br)([Br:16])=O.O>C(#N)C>[Br:16][C:4]1[C:5]2[C:6](=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[N:2]([CH3:1])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 210980271-Methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-ol

Product 1

HCID 210980543-bromo-1-methyl-6-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidineYield 61.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

1-Methyl-6-methylsulfanyl-1,2-dihydro-pyrazolo[3,4-d]pyrimidin-3-one (2.0 g, 0.01 mol) was refluxed with phosphorus oxybromide (6 g) in acetonitrile (60 mL). Water (100 mL) was then added and the reaction mixture cooled to 5° C., hold for 1 hour and filtered to give 1.6 g (61%) of pure 3-bromo-1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine; 1H-NMR (DMSO): δ 2.61 (s, 3H), 3.96 (s, 3H), 9.00 (s, 1H), LC/MS (m/e)=260.8 (MH+), Rt=1.89 min.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-a97bc2e84bb84d918eeb8164374b07b5
Source dataset
uspto-grants-2007_05
Patent number
US07217710B2

Reaction notes

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