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With N-iodo-succinimide; In chloroform; for 2.0h;Reflux;
To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.3 g, 9.7 mmol, 1.0 eq) in CHC13 (45 mL) was added NIS (2.18 g, 9.7 mmol, 1.0 eq) at rt. The solution was refluxed for 2 h. The precipitate was filtered and dried in vacuo to give 5-iodo-7H- pyrrolo[2,3-d]pyrimidin-4-ylamine (2.09 g, 83%) as a white solid.
82.51%
With N-iodo-succinimide; In acetonitrile; at 120℃; for 24.0h;
4-Amino-7H-pyrrolo [2,3-d] pyrimidine (0.60 g, 4.47 mmol) was weighedN-iodosuccinimide (1.51 g, 6.71 mmol)Dissolved in 100 ml of acetonitrile,And heated at 120 for 24h.After the reaction is completed, the solvent is evaporated,With dichloromethane mixed with water extraction,The organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure.The residue was purified by column chromatography to give 0.96 g of a yellow solid (82.51% yield).
80%
With N-iodo-succinimide; In chloroform; for 2.0h;Reflux;
1.3 g (9.7 mmol) of 7H-pyrrolo[2,3-d]pyrimidino-4-amine were suspended in 30 mL of chloroform and 2.18 g (9.7 mmol) of N-iodosuccinimide were added. The reaction mixture was refluxed for 2 hours, then the precipitated collected by filtration. The product was purified by a silica gel column eluted by DCM/MeOH 95/5, affording 2.02 g (80%) of the title compound.
73%
With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; for 3.0h;Cooling with ice;
7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.4 g, 3.0 mmol) was dissolved in 10 mL DMF.NIS (0.74 g, 3.3 mmol) was added in portions under ice bath.After the feeding is completed, the ice bath is removed.The reaction was allowed to proceed at room temperature for 3 hours, and the reaction was confirmed to be complete by TLC. 20 mL of water was added to the reaction solution.It was extracted with ethyl acetate (30 mL*3), and the organic phase was washed with 20 mL of brine.Dry over anhydrous sodium sulfate, concentrate,The residue was separated into a pale yellow solid (0.56 g).The yield was 73%.
With N-iodo-succinimide; In chloroform; for 2.0h;Reflux;
[0820] Example 6: 5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine (I8): . In a 20mL scintillation vial, purchased pyrrolopyrimidine (1g, 7.45mmol) was dissolved in 7mL of chloroform. NIS (2.18g, 9.69mmol) was added and reaction was refluxed for 2 hours. Upon cooling, precipitate was filtered to yield intermediate I8. LC-MS (ES+) calcd for C6H5IN4 (M+H)+ 260.96, found 260.61.
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