4-chloro-6,7- dihydro-5H-pyrrolo[2,3-d]pyrimidine
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![4-chloro-6,7- dihydro-5H-pyrrolo[2,3-d]pyrimidine structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/ac2395fcfdeb4714998fa3f3dea9a1ea.png "4-chloro-6,7- dihydro-5H-pyrrolo[2,3-d]pyrimidine")
4-chloro-6,7- dihydro-5H-pyrrolo[2,3-d]pyrimidine
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CAS No:
16372-08-0
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Formula:
C6H6ClN3
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Chemical Name:
4-chloro-6,7- dihydro-5H-pyrrolo[2,3-d]pyrimidine
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Synonyms:
4-Chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine;5H-Pyrrolo[2,3-d]pyrimidine, 4-chloro-6,7-dihydro-;5H-Pyrrolo[2,3-d]pyrimidine,4-chloro-6,7-dihydro-;SCHEMBL3803152;CTK4D1631;KS-00000HIJ;DTXSID50671981;ANW-48992;MFCD11518925;ZINC35269948
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CAS No:
4-chloro-6,7- dihydro-5H-pyrrolo[2,3-d]pyrimidine Use and Manufacturing
General procedure: A mixture of dimethyl-[2-piperazin-1 -yl-2-(4-trifluoromethyl-phenyl)-ethyl]-amine (300.00 mg; 0.96 mmol; 1 .00 eq.), 4-Chloro-6, 7-dihydro-5H-pyrrolo[2, 3-d]pyrimidine (156.52 mg; 0.96 mmol; 1 .00 eq.) and potassium carbonate (336.95 mg; 2.39 mmol; 2.50 eq.) in dry DMSO (3.00 ml) was irradiated at 1 90 °C for 3h. The reaction mixture was cooled to RT, diluted with water (25 ml_), and extracted with DCM (3 x 10ml). The combined organic layer was washed with water, brine solution, dried over Na2S04 and concentrated under vacuum. The resulted brown thick residue was purified by biotage using DCM/MeOH as an elutent to yield brown gum. This gum was further azeotroped with diethylether (2 x 10ml) to obtain foamy solid. Then this solid was further treated with diethyl ether/hexane mixture (1 :1 , 5ml). The solventportion was syringed out and the remaining solid was further dried under vacuum to afford the title compound as pale brown solid (34.00 mg, 8.2 percent yield). LC- MS (M+H = 421 , obsd. = 421 ); 1 H NMR (400 MHz, DMSO-d6) delta [ppm]: 7.80 (s, 1 H), 7.67 (d, J = 7.7 Hz, 2H), 7.50 (d, J = 8.1 Hz, 2H), 6.56 (bs, 1 H), 3.76 (s, 1 H), 3.50-3.48 (m, 4H), 3.37 (bs, 2H), 3.01 (t, J = 8.6 Hz, 2H), 2.79 (bs, 2H), 2.50-2.49 (m, 1 H), 2.39 (bs, 4H), 2.10 (bs, 6H).
4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine is a pyrolopyrimidine derivative used in the preparation of the antibiotic tubercidin (7-deazadenosine).
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4-chloro-6,7- dihydro-5H-pyrrolo[2,3-d]pyrimidine
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