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Water → 3-(6-bromo-pyridin-2-yl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine

HRID 1809702
Notes
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Reaction equation

HRID 1809702 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][C:22]1[N:27]=[C:26]([C:28]2[C:36]3[C:31](=[N:32][C:33]([Cl:37])=[N:34][CH:35]=3)[NH:30][N:29]=2)[CH:25]=[CH:24][CH:23]=1.CCN(CC)CC.O>CN(C=O)C>[Br:21][C:22]1[N:27]=[C:26]([C:28]2[C:36]3[C:31](=[N:32][C:33]([Cl:37])=[N:34][CH:35]=3)[N:30]([C:1]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:29]=2)[CH:25]=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178478327HCID 178478327, compound

Product 1

HCID 866679613-(6-bromo-pyridin-2-yl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

A solution of trityl chloride (8.5 g, 30.5 mmol) in DMF (80 mL) was added dropwise to the solution of 3-(6-bromo-pyridin-2-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine (from Example 30 supra) (8.0 g, 25.7 mmol) and Et3N (12 mL, 83.2 mmol) in DMF (100 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 hours then poured into water and extracted with ethyl acetate. The organic solution was dried with anhydrous Na2SO4. After filtration and concentration, the residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate, 20:1) to give 3-(6-bromo-pyridin-2-yl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine as a white powder. (Yield 3.8 g, 27%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried with anhydrous Na2SO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate, 20:1)

Sources & evidence

ORD record
ord-60e00282b3874177b4fa88c7a03cdb69
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362023B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes