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Product Details of 6-Chloro-7-iodo-7-deazapurine

CAS No. :123148-78-7
Formula : C6H3ClIN3
M.W : 279.47
SMILES Code : ClC1=NC=NC2=C1C(=C[NH]2)I
MDL No. :MFCD09263258
InChI Key :CBWBJFJMNBPWAL-UHFFFAOYSA-N
Pubchem ID :14809281

Safety of 6-Chloro-7-iodo-7-deazapurine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 6-Chloro-7-iodo-7-deazapurine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 123148-78-7 ]

[ 123148-78-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 123148-78-7 ]
  • [ 163226-45-7 ]
  • [ 934815-82-4 ]
YieldReaction ConditionsOperation in experiment
93% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 0.5h; To a mixture of compound 1 (380 mg, 0.89 mmol), compound 5 (310 mg, 1.11 mmol) and Ph3P (467 mg, 1.78 mmol) in THF (40 mL) was added DIAD (360 mg, 1.78 mmol) at 0 0C. After stirring 30 min at rt, the mixture was evaporated and purified by column chromatography on a silica gel to give 14 (580 mg, 93 %) as a white solid, mp : 94 - 95 C; [Cc]24D -33.50 (c 0.26, CHCl3); 1H NMR (500 MHz, CDCl3) delta 8.68 (s, IH), 7.45 - 7.50 (m, 6H), 7.25 - 7.35 (m, 9H), 7.17 (s, IH), 5.99 (d, J= 2.0 Hz, IH), 5.90 (s, IH), 5.20 (d, J= 5.0 Hz, IH), 4.55 (d, J= 6.0 Hz, IH), 4.07 (d, J= 15.5 Hz, IH), 3.88 (d, J= 15.5 Hz, IH), 1.45 (s, 3H), 1.31 (s, 3H); 13C NMR (125 MHz, CDCl3) 152.80, 151.14, 150.52, 150.49, 143.73, 132.17, 128.56, 128.02, 127.32, 121.92, 117.49, 112.79, 87.44, 84.80, 83.95, 65.33, 61.52, 51.29, 27.51, 26.07. UV (CHCl3) lambdamax310, 267, 224 nm.
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 0.5h; To a mixture of compound 1 (380 mg, 0.89 mmol), compound 5 (310 mg, 1.11 mmol) and Ph3P (467 mg, 1.78 mmol) in THF (40 mL),was added DIAD (360 mg, 1.78 mmol) at 0 0C. After stirring 30 min at rt, the mixture was evaporated and purified by column chromatography on a silica gel to give a white solid (580 mg). A portion of solid (550 mg) was treated with saturated methanolic ammonia and heated to 80 C for 16h. After cooling, the mixture was purified by column chromatography on a silica gel to give 9 (545 mg, 94 %) as a white solid, mp : 114 - 116 C; [alpha]27D -34.68 (c 0.34, CHCl3); 1H NMR (500 MHz, CDCl3) delta 8.34 (s, IH), 7.4 - 7.5 (m, 6H), 7.2 - 7.35 (m, 9H), 6.84 (s, IH), 6.00 (s, IH), 5.85 (s, IH), 5.71 (br s, 2H), 5.18 (d, J= 5.5 Hz, IH), 4.54 (d, J= 6.0 Hz, IH), 4.03 (d, J= 15.0 Hz, IH), 3.85 (d, J= 16.0 Hz, IH), 1.44 (s, 3H), 1.30 (s, 3H); 13C NMR (125 MHz, CDCl3) 156.93, 152.63, 150.16, 149.56, 143.82, 128.59, 127.98, 128.00, 127.26, 126.41, 122.77, 112.55, 104.59, 87.31, 85.03, 83.98, 64.64, 61.58, 49.36, 27.56, 26.14. UV (CHCl3) lambdamax 287.0 nm; Anal. Calcd. for (C34H31IN4O3-O^CHCl3) C 58.57, H 4.48, N 7.97 Found C 58.52, H 4.56, N 7.98.
  • 3
  • [ 123148-78-7 ]
  • [ 109431-87-0 ]
  • tert-butyl (S)-3-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -10 - 25℃;Inert atmosphere; To a stirred solution of 11a (10.11 g, 36.18 mmol), (R)-tert-butyl3-hydroxypyrrolidine-1-carboxylate (13.55 g, 72.35mmol) and PPh3 (17.08 g, 65.12 mmol) in anhydrous THF (200 mL) was slowly added DIAD (10.97 g, 54.26 mmol) over 1 h at -10 C and under N2 atmosphere. The resulting reaction mixture was subsequently warmed up to rt and stirred overnight. The solvent was evaporated and the residue was purified by a flash column to give the product 13a as white solid (9.87 g, 60% yield). 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 7.39 (s, 1H), 5.47 (br. s, 1H), 3.90 (dd, J 11.5, 6.8 Hz,1H), 3.62-3.58 (m, 3H), 2.45 (td, J 13.9, 7.4 Hz, 1H), 2.25 (td,J 13.0, 6.4 Hz, 1H), 1.50 (s, 9H). HRMS-ESI: calcd for C15H19N4O2Cl[M+H]+ 449.0241, found: 449.0244. Intermediate 13b -k was synthesized by the corresponding chiral alcohol compounds and 11a following the procedure of preparation 13a.
60% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -10 - 20℃;Inert atmosphere; To a stirred solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (10.1 g, 36.2 mmol), (R)- tert-butyl3-hydroxypyrrolidine-1-carboxylate (13.6 g, 72.4 mmol) and PPh3 (17.1 g, 65.1 mmol) in anhydrous THF (200 mL) was slowly added DIAD (10.9 g, 54.2 mmol) over 1h at -10 C and under nitrogen atmosphere. The resulting reaction mixture was subsequently warmed up to room temperature and stirred overnight. The solvent was evaporated and the residue was purified by a flash (PE/EA = 5/1) to give (S)-tert-butyl 3-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7- yl)pyrrolidine-1-carboxylate (9.9 g, 60%) as a white solid. [M+H] Calcd.: 449.0, found: 449.0
60% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -10 - 20℃;Inert atmosphere; To a stirred solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (10.1 g, 36.2 mmol), (R)- tert-butyl3-hydroxypyrrolidine-1-carboxylate (13.6 g, 72.4 mmol) and PPh3 (17.1 g, 65.1 mmol) in anhydrous THF (200 mL) was slowly added DIAD (10.9 g, 54.2 mmol) over 1h at -10 C and under nitrogen atmosphere. The resulting reaction mixture was subsequently warmed up to room temperature and stirred overnight. The solvent was evaporated and the residue was purified by a flash (PE/EA = 5/1) to give (S)-tert-butyl 3-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7- yl)pyrrolidine-1-carboxylate (9.9 g, 60%) as a white solid. [M+H] Calcd.: 449.0, found: 449.0
1.04 g With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 1h; DIAD (1.41 ml) was added to a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.00 g), (R)-N-Boc-3-pyrrolidinol (1.01 g), and triphenylphosphine (1.88 g) in tetrahydrofuran (40 ml), and the reaction mixture was stirred for 1 hour. The reaction mixture was concentrated and washed with ethyl acetate to obtain the title compound as a white solid (1.04 g). Physical properties: m/z[M+H]+ 448.9
1.04 g With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 1h; DIAD (1.41 ml) was added to a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.00 g), (R)-N-Boc-3-pyrrolidinol (1.01 g), and triphenylphosphine (1.88 g) in tetrahydrofuran (40 ml), and the reaction mixture was stirred for 1 hour. The reaction mixture was concentrated and washed with ethyl acetate to obtain the title compound as a white solid (1.04 g). Physical properties: m/z[M+H]+ 448.9
1.04 g With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 1h; DIAD (1.41 ml) was added to a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.00 g), (R)-N-Boc-3-pyrrolidinol (1.01 g), and triphenylphosphine (1.88 g) in tetrahydrofuran (40 ml), and the reaction mixture was stirred for 1 hour. The reaction mixture was concentrated and washed with ethyl acetate to obtain the title compound as a white solid (1.04 g). Physical properties: m/z [M+H]+ 448.9

  • 4
  • [ 123148-78-7 ]
  • [ 163622-50-2 ]
  • 5
  • [ 123148-78-7 ]
  • [ 199174-24-8 ]
  • (R)-tert-butyl 3-((4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -10 - 25℃;Inert atmosphere; General procedure: To a stirred solution of 11a (10.11 g, 36.18 mmol), (R)-tert-butyl3-hydroxypyrrolidine-1-carboxylate (13.55 g, 72.35mmol) and PPh3 (17.08 g, 65.12 mmol) in anhydrous THF (200 mL) was slowly added DIAD (10.97 g, 54.26 mmol) over 1 h at -10 C and under N2 atmosphere. The resulting reaction mixture was subsequently warmed up to rt and stirred overnight. The solvent was evaporated and the residue was purified by a flash column to give the product 13a as white solid (9.87 g, 60% yield).
  • 6
  • [ 123148-78-7 ]
  • [ 477293-60-0 ]
  • tert-butyl (2S,4R)-4-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.5 g tert-Butyl (2S,4S)-4-hydroxy-2-methylpyrrolidine-1-carboxylate (19.0 g) and 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (13.1 g) were dissolved in THF (190 mL), and the obtained solution was then cooled to 0 C. Thereafter, triphenylphosphine (37.2 g) and diisopropyl azodicarboxylate (28.1 mL) were added to the reaction solution, and the temperature of the mixture was then increased to room temperature, followed by stirring for 1 hour. Thereafter, the reaction mixture was concentrated under reduced pressure, and the obtained residue was then purified by silica gel chromatography (hexane:ethyl acetate) to obtain the corresponding coupling body. The obtained compound was used in the subsequent reaction without being further purified. The obtained coupling body, THF (114 mL) and ammonia water (114 mL) were added into a pressure resistant tube, and the obtained mixture was then stirred at 100 C. for 14 hours. Thereafter, the reaction mixture was cooled to room temperature, and was then poured into water (285 mL). The thus obtained mixture was stirred at room temperature for 5 hours. Thereafter, the precipitated solid was collected by filtration, was then washed with water, and was then dried to obtain a product of interest (34.5 g). 1HNMR (CDCl3) δ: 8.27 (s, 1H) 7.15 (s, 1H) 5.55-5.73 (m, 2H) 5.12-5.25 (m, 1H) 3.86-4.18 (m, 2H) 3.43-3.57 (m, 1H) 2.59-2.69 (m, 1H) 1.92-2.03 (m, 1H) 1.48 (s, 9H) 1.30-1.40 (m, 3H) ESI-MS m/z 444 (MH+)
 

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