Ammonium Hydroxide → 3-chloro-1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 1351147Notes

Reaction equation

HRID 1351147 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(Cl)(Cl)([Cl:16])=O.[OH-].[NH4+]>>[Cl: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

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 210980271-Methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-ol

Product 1

HCID 2959223-chloro-1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidineYield 61%

Procedure

1-Methyl-6-methylsulfanyl-1,2-dihydro-pyrazolo[3,4-d]pyrimidin-3-one (2.0 g, 0.01 mol) was heated with phosphorus oxychloride (8 mL) in a sealed tube at 140° C. for 6 hours. The reaction mixture was then poured into ice-water and basified with ammonium hydroxide. The formed product was isolated by filtration. The crude product was recrystalized from a 1:1 ethanol-water mixture to give 1.3 g (61%) of pure 3-chloro-1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine; LC/MS (m/e)=215.0 (MH+), Rt=1.94 min.

Workup

  1. customThe formed product was isolated by filtration
  2. customThe crude product was recrystalized from a 1:1 ethanol-water mixture

Sources & evidence

ORD record
ord-2628f582cc4a4a7aa13383ba87bac024
Source dataset
uspto-grants-2007_05
Patent number
US07217710B2

Reaction notes

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