Trityl chloride → 3-iodo-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 897771Notes

Reaction equation

HRID 897771 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]1([C:24](Cl)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([C:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chloride2×HCID 10796Cesium carbonate2×HCID 178508725HCID 178508725, compound

Product 1

HCID 223468963-iodo-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (3.0 g, 11.5 mmol) in dimethylformamide (50 mL) was treated with cesium carbonate (5.62 g, 17.25 mmol) and triphenylmethyl chloride (3.85 g, 13.8 mmol). The reaction mixture was stirred at 70° C. for 22.5 h under a nitrogen atmosphere. Cesium carbonate (3.75 g, 11.5 mmol) and triphenylmethyl chloride (3.2 g, 11.5 mmol) were added to the reaction mixture and was stirred for 6.5 h. The reaction mixture was added to ice water. The precipitate was filtered and washed with water. The product, 3-iodo-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, was dried over night on the lyophilizer. The resulting solid was triturated with ethyl acetate to give 3.05 g (53%) of 3-iodo-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. 1H NMR (DMSO-d6, 400 MHz) δ 7.3190-7.1106 (m, 16H); TLC (Baker Pre-coated Hard Layer Silica Gel TLC plates, Si250F254, 30% Ethyl acetate in heptane) Rf=0.33.

Workup

  1. stirringwas stirred for 6.5 h
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. dry with materialThe product, 3-iodo-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, was dried over night on the lyophilizer
  5. customThe resulting solid was triturated with ethyl acetate

Sources & evidence

ORD record
ord-7e1cd0e47b1f4ecc8742c07218c6418c
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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