Preparation method and applications of pyrrolopyrimidine compound
A compound, unsubstituted technology, applied in the application field of immunosuppressants, which can solve problems such as combined immunodeficiency disease
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[0084] The preparation of formula I-b compound
[0085] The present invention also provides a method for preparing a representative compound I-b of the compound of formula I, said method comprising the steps of:
[0086]
[0087] In an inert solvent, the compound of formula II is reacted with the compound of formula III to obtain the compound of formula I-b, wherein, R 1 ’ is defined as above.
[0088] In another preferred embodiment, the inert solvent is selected from the group consisting of dichloromethane, chloroform, 1,2-dichloroethane, toluene, xylene, or combinations thereof.
[0089] In another preferred example, the molar ratio of the compound of formula II to the compound of formula III is 0.5-2:0.5-2; preferably about 1:1.
[0090] In another preferred example, the reaction time is 1-15h, preferably 2-10h, more preferably 0.5-5h.
[0091] In another preferred example, the reaction is carried out under an organic base catalyst.
[0092] In another preferred emb...
Embodiment 1
[0114] Example 1 Preparation of compound 1: N-methyl-N-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl-1,4-diamine
[0115]
[0116] Weigh 1.53 g of 4-chloropyrrolopyrimidine, 4.6 g of N-methyl-p-nitroaniline, and 4M HCl in dioxane and heat in 40 mL of dioxane at 130° C. overnight. The mixture was cooled to room temperature and concentrated to dryness under reduced pressure. The residue was slurried with ethyl acetate until most of the N-methyl-p-nitroaniline disappeared, and the resulting solid was dissolved in a mixture of methanol and triethylamine (1.5 eq), added to silica gel, and concentrated to dryness under reduced pressure. The residue was separated by silica gel column chromatography and eluted with dichloromethane / methanol=30 / 1 system to obtain 1.4 g of N-methyl-N-(4-nitrophenyl)-7H-pyrrolo[2,3-d ] Pyrimidin-4-amine, yield 91.5%.
[0117] 11g of the above product, 10% Pd / C, was stirred in a methanol closed system equipped with a hydrogen balloon until the raw materials...
Embodiment 2
[0121] Example 2 Preparation of compound 2: 5-methyl-isoxazole-{4-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-phenyl}-4- Amide
[0122] Weigh 100mg N-methyl-N-(7H-pyrrolo[2,3-d]pyrimidine-4-)phenyl-1,4-diamine and 16mg DMAP respectively in a three-necked flask, add 20mL dichloromethane Stir to dissolve, cool to about -20°C, and add 100 mg of triethylamine dropwise to the reaction solution. Then, 103 mg of 5-methylisoxazole-4-carbonyl chloride dissolved in 5 mL of dichloromethane solution was slowly added dropwise. After the dropwise addition, the mixture was slowly raised to room temperature and reacted for 5 hours. The reaction was monitored by TLC until the end. Add 20mL of water to quench the reaction, separate and extract, wash the aqueous phase with dichloromethane 3 times, combine the organic phase, anhydrous Na 2 SO 4 Dry and separate by silica gel column chromatography, eluting with ethyl acetate / n-hexane = 1 / 1 system to obtain 72 mg of the product with a yield ...
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