Water → 3-(3-bromo-phenyl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine

HRID 1809710Notes

Reaction equation

HRID 1809710 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][C:13]([Cl:17])=[N:14][CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[C:25](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][C:13]([Cl:17])=[N:14][CH:15]=3)[N:10]([C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178478326HCID 178478326, compound

Product 1

HCID 866679653-(3-bromo-phenyl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 3-(3-bromo-phenyl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine (from Example 38 supra) (4.0 g, 12.9 mmol) and Et3N (2.6 g, 25.8 mmol) in DMF (40 mL) was added the solution of trityl chloride (4.3 g, 15.5 mmol) in DMF (40 mL) at room temperature. This mixture was stirred at room temperature for 2 hours. The reaction solution was then poured into water (400 mL), and the yellow precipitate was collected by filtration. This crude product was purified by chromatography (silica gel, dichloromethane:petroleum ether, 1:1) to give 3-(3-bromo-phenyl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine as a light yellow solid. (Yield 3.5 g, 30%).

Workup

  1. filtrationthe yellow precipitate was collected by filtration
  2. customThis crude product was purified by chromatography (silica gel, dichloromethane:petroleum ether, 1:1)

Sources & evidence

ORD record
ord-424b570a0cd54ebdb5f740742d04594a
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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