Related Products of 35808-68-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 35808-68-5, name is 4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.
To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (500 mg, 3.27 mmol) in DMF (5 mL) caesium carbonate (2.13 g, 6.54 mmol) and benzensulfonyl chloride (417 mu, 3.27 mmol) were added. The mixture was stirred at room temperature for 1.5 hours, then diluted with ethylacetate and washed with water and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The residue was chromatographed on a silica gel column eluted with dichloroethane/ethylacetate 7/3 affording 761 mg (79%) of 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (cmpd (XVIII), step h). To a solution of 2M in THF lithium diisopropylamide (0.83 mL, 1.65 mmol) in dry THF (5 mL) cooled to -78C, under argon atmosphere, the last intermediate (400 mg, 1.37 mmol) dissolved in 5 mL of dry THF, was added dropwise during 10 minutes. The mixture was maintained in these conditions for 1 hour and then methyl iodide was added (0.11 mL, 1.78 mmol). The mixture was stirred 2 hours and during this time further 0.21 mL of methyl iodide were added. After 4 hours the temperature was driven to -10C and a saturated aqueous solution of ammonium chloride was added. The product was then extracted with ethylacetate, the organic layer dried over Na2S04 and evaporated affording 4-chloro-6-methyl-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (cmpd (XX), step i). This intermediate (1.37 mmol) was dissolved in 10 mL of THF and 5 mL of methanol and 0.5 g of sodium hydrate were added. The mixture was stirred at room temperature for 1 hour, then the solvent removed in vacuo. The residue was taken up with ethylacetate and washed with a saturated aqueous solution of ammonium chloride and extracted again with ethylacetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated, .giving 223 mg of 4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (cmpd (XXI), step j). This intermediate (1.37 mmol) was dissolved in chloroform (10 mL) and N-iodo succinimide (308 mg, 1.37 mmol) was added. The mixture was refluxed for 1.5 hours, cooled to room temperature, diluted with dichloromethane, washed with aqueous Na2S203 and ammonium chloride. The organic layer was dried over Na2S04 and evaporated. The residue was chromatographed on a silica gel column 1 ,2-dichloroethane/ethylacetate 6/4, giving 110 mg of 4-chloro- 5- iodo-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (cmpd (XXII), step d). The last intermediate (0.39 mmol) was dissolved in DMF (3 mL) and additioned with caesium carbonate (257 mg, 0.79 mmol) and iodoethane (47 mu, 0.59 mmol). The mixture was stirred at room temperature for 2 hours, thenpoured into water and extracted twice with ethylacetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was finally puriufied by chromatography on a silica gel column eluted with dichloromethane/ethylacetate giving 51 mg of 4-chloro-7-ethyl-5-iodo-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (cmpd (IV), step e). 1H NMR (401 MHz, DMSO-d6) delta ppm 1.24 – 1.32 (m, 3 H) 2.54 (s, 3 H) 4.36 (q, J=7.16 Hz, 2 H) 8.58 (s, 1 H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,35808-68-5, its application will become more common.
Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; ANGIOLINI, Mauro; BUFFA, Laura; MENICHINCHERI, Maria; MOTTO, Ilaria; POLUCCI, Paolo; TRAQUANDI, Gabriella; ZUCCOTTO, Fabio; WO2014/184069; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
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