Water → HCID 90408799, compound

HRID 1521679Notes

Reaction equation

HRID 1521679 reaction equation
S(Cl)(Cl)=O.O[CH2:6][C:7]([NH:10][C:11]1[N:12]([CH3:29])[C:13](=[O:28])[C:14]2[C:15](=[N:17][N:18]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=3)[CH:19]=2)[N:16]=1)([CH3:9])[CH3:8].O.[OH-].[NH4+]>CN(C=O)C>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:18]2[CH:19]=[C:14]3[C:13](=[O:28])[N:12]([CH3:29])[C:11]4[N:16]([CH2:6][C:7]([CH3:9])([CH3:8])[N:10]=4)[C:15]3=[N:17]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 90408487HCID 90408487, compound

Product 1

HCID 90408799HCID 90408799, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (67 mL, 922 mmol) is added dropwise to a solution of 6-(1-hydroxy-2-methylpropan-2-ylamino)-5-methyl-2-(4-bromobenzyl)-2H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (134 g, 330 mmol) in DMF (800 mL). The reaction mixture is stirred at room temperature until the reaction is complete. The mixture is poured into cold water, and then adjusted to pH 8-9 with ammonium hydroxide aqueous solution. After filtration, the obtained solids are washed with water, and then dried under vacuum to give 118 g of product (yield: 92%). MS (ESI) 388.1 [M+H]+.

Workup

  1. filtrationAfter filtration
  2. washthe obtained solids are washed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-baf618cc872e40109b21a10b32554f6b
Source dataset
uspto-grants-2015_07
Patent number
US09073936B2

Reaction notes

Loading…