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[ CAS No. 123148-78-7 ] {[proInfo.proName]}

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Chemical Structure| 123148-78-7
Chemical Structure| 123148-78-7
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Product Details of [ 123148-78-7 ]

CAS No. :123148-78-7 MDL No. :MFCD09263258
Formula : C6H3ClIN3 Boiling Point : -
Linear Structure Formula :- InChI Key :CBWBJFJMNBPWAL-UHFFFAOYSA-N
M.W : 279.47 Pubchem ID :14809281
Synonyms :

Calculated chemistry of [ 123148-78-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.62
TPSA : 41.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 2.27
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.7
Log Po/w (SILICOS-IT) : 3.18
Consensus Log Po/w : 2.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.61
Solubility : 0.0689 mg/ml ; 0.000246 mol/l
Class : Soluble
Log S (Ali) : -2.78
Solubility : 0.464 mg/ml ; 0.00166 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.1
Solubility : 0.0221 mg/ml ; 0.0000791 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.86

Safety of [ 123148-78-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 123148-78-7 ]

* 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.

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

[ 123148-78-7 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 123148-78-7 ]
  • [ 2179-92-2 ]
  • [ 24391-41-1 ]
Reference: [1] Patent: WO2010/15637, 2010, A1, . Location in patent: Page/Page column 96
  • 2
  • [ 3680-69-1 ]
  • [ 123148-78-7 ]
YieldReaction ConditionsOperation in experiment
100% With N-iodo-succinimide; sodium sulfate In ethanol; N,N-dimethyl-formamide Step 1.
4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (Compound 3)
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75g (70 mmol) (Toronto Research Chemicals, Inc) and N-iodosuccinimide (16.8g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night.
The solvent was evaporated.
The yellow residue was suspended in hot 10percent solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6percent) of the title compound as off-white crystals.
The mother liquid was evaporated up to 1/3 volume and crystallized again from ethanol to give 2.47 g (12.3percent) of the title product.
Total yield is close to 100percent.
100% With N-iodo-succinimide; sodium sulfate In ethanol; N,N-dimethyl-formamide Step 1.
4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (Compound 3)
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) (Toronto Research Chemicals, Inc) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night.
The solvent was evaporated.
The yellow residue was suspended in hot 10percent solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6percent) of the title compound as off-white crystals.
The mother liquid was evaporated up to 1/3 volume and crystallized again from ethanol to give 2.47 g (12.3percent) of the title product;
Total yield is close to 100percent; M.p. 212-214 (decomposition); UV λmax: 307, 266, 230, 227 nm (methanol); MS: 277.93 (M-H), 313 (M+Cl); 1H-NMR (DMSO-d6): 12.94 (s, 1H, NH), 8.58 (s, 1H, H-2), 7.94 (s, 1H, H-8).
100% With N-iodo-succinimide; sodium sulfate In ethanol; N,N-dimethyl-formamide Step 1.
4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night.
The solvent was evaporated.
The yellow residue was suspended in hot 10percent solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6percent) of the title compound as off-white crystals.
The mother liquid was evaporated up to 1/3 volume and crystallize again from ethanol to give 2.47 g (12.3percent) of the title product;
Total yield is close to 100percent;
Tm:
212-214 (decompose);
UV λmax: 307, 266, 230, 227 nm (methanol);
MS: 277.93 (M-H), 313 (M+Cl);
1H-NMR (DMSO-d6): δ 12.94 (s, 1H), 8.58 (s, 1H), 7.94 (s, 1H).
100% With N-iodo-succinimide; sodium sulfate In ethanol; N,N-dimethyl-formamide Step 1.
4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75g (70 mmol) and N-iodosuccinimide (16.8g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night.
The solvent was evaporated.
The yiellow residue was suspended in hot 10percent solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6percent) of the title compound as off-white crystals.
The mother liquid was evaporated up to 1/3 volume and crystallized again from ethanol to give 2.47 g (12.3percent) of the title product.
The total yield is close to 100percent;
Tm 212-214° C. (dec);
UV λmax: 307, 266, 230, 227 nm (methanol);
MS: 277.93 (M-H), 313 (M+Cl);
1H-NMR (DMSO-d6): 12.94 (s, 1H, NH), 8.58 (s, 1H, H-2), 7.94 (s, 1H, H-8).
100% With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; Step 1To a solution of 4-chloro-7H-pyrro]o[2,3-d]pyrimidine (8.0 g , 52.32 mmol, 1.0 eq) in DMF (40 raL), NiS ( 15.7g , 57.55 mmol, 1.1 eq) was added at 0° C. The reaction mixture was stirred overnight at room temperature. Water (40 rnL) was added to the reaction mixture, extracted with EtOAc. The organic layer was dried over Na2S04 and concentrated under vacuum to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (14.6 g, 100 percent in yield).
100% With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; Step 1To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (8.0 g , 52.32 mmol, 1.0 eq) in DMF (40 mL), NIS ( 15.7g , 57.55 mmol, 3.1 eq) was added at 0° C. The reaction mixture was stirred overnight at room temperature. Water (40 mL) was added to the reaction mixture, extracted with EtOAc. The organic layer was dried over Na2S(3/4 and concentrated under vacuum to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (14.6 g, 100 percent in yield)
100% With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; Step 1. To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (8.0 g, 52.32 mmol, 1.0 eq) in DMF (40 mL), NIS (15.7g,57.55 mmol, 1.1 eq) was added at 0° C. The reaction mixture was stirred overnight at room temperature. Water (40 mL) was added to the reaction mixture,extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under vacuum to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (14.6 g, 100 percent in yield).
100% With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; Step 1
To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (8.0 g, 52.32 mmol, 1.0 eq) in DMF (40 mL), NIS (15.7 g, 57.55 mmol, 1.1 eq) was added at 0° C.
The reaction mixture was stirred overnight at room temperature.
Water (40 mL) was added to the reaction mixture, extracted with EtOAc.
The organic layer was dried over Na2SO4 and concentrated under vacuum to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (14.6 g, 100percent in yield).
100% With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (8.0 g, 52.32 mmol, 1.0 eq) was dissolved in DMF (40 mL), NIS (15.7 g, 57.55 mmol, 1.1 eq) was added at 0°C, stirred overnight at room temperature, 200 mL of saturated Na2S2O3 solution was added, filtered, washed with water three times, and dried in vacuum to obtain 14.6 g (100percent) of products. 1H NMR (400 MHz, d6-DMSO): δ 12.94 (s, 1H), 8.59 (s, 1H), 7.93 (d, J = 2.4 Hz, 1H).
99% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 1 h; A solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (201) (500 mg, 3.25 mmol) and NIS (805 mg, 1.1 eq, 3.6 mmol) in DMF (1 mL) was stirred at room temperature for 1 h. The mixture was concentrated in vacuo, then water (10 mL) was added. The resulting solid was collected by filtration. Then dried in vacuo to afford the desired product, 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (202) (900 mg, 99percent yield) as a off-white solid. ESI-MS m/z: 277.85 [M−H]. The product obtained was used directly in the next step without purification.
95% With N-iodo-succinimide In N,N-dimethyl-formamide for 20 h; Inert atmosphere; Darkness To a dry 250 mL round bottomed flask under argon was added 1.8 g (11.9 mmol) of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine and 3.0 g of N-iodosuccinamide (13.1 mmol). The solids were dried under high vacuum for 5 hours and the flask was refilled with argon. Dry DMF (100 mL) was added and the solution was stirred in the dark for 20 hours. The reaction was quenched with methanol and concentrated. The residue was then diluted with 150 mL of dichloromethane and washed with water (200 mL), saturated aqueous sodium sulfite (200 mL), and brine (100 mL). The organic layers were dried over MgSO4, filtered, and concentrated. The column was run using 1:1 Hex/EtOAc as the eluent to give a white solid (3.1 g, 11.2 mmol, 95percent yield). (Rf: 0.22; 1:1 Hex/EtOAc). mp: 195 - 199 °C (decomposition). 1H-NMR ([(CD3)2SO], 600 MHz): σ 7.94 (s, 1H), 8.59 (s, 1H). 13C-NMR ([(CD3)2SO], 150 Mz): σ 51.7, 115.8, 133.9, 150.4, 150.7, 151.5. HRMS (FAB): expected for C6H3ClN3I (M+H)+: 279.91329. Found: 279.91316. IR(neat): vmax 3061, 2819, 1593, 1158 cm-1. Elemental Analysis for C6H3ClIN3: Found: C, 26.33; H, 1.13; N: 14.94. Calculated: C, 25.79; H, 1.08; N, 15.04.
95% With N-iodo-succinimide In N,N-dimethyl-formamide for 25 h; Inert atmosphere; Darkness 4-Chloro-5-iodo-7H-pyrrolo[2,3]pyrimidine 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (1.8 g 11.9 mmol) and N- iodosuccinamide (3g, 13.1 mmol) were mixed in a round bottomed flask. The flask was dried under high vacuum for 5 h and then back-filled with argon. To this mixture, dry DMF (100 mL) was added and the resulting mixture was stirred in the dark for 20 h. The reaction was quenched with methanol and concentrated in vacuo. The residue was diluted with 150 mL of DCM and washed with water (200 mL), saturated aqueous sodium sulfite (200 mL), and brine (100 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (50percent ethyl acetate / hexanes) to afford the desired product (3.1 g, 95percent yield) as a white solid. ESI-MS m/z: 279.5 [M + H]+.
95% With N-iodo-succinimide In N,N-dimethyl-formamide for 20 h; Inert atmosphere; Darkness 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (1.8 g 11.9 mmol) and Niodosuccinamide (3g, 13.1 mmol) were mixed in a round bottomed flask. The flask was dried under high vacuum for 5 h and then back-filled with argon. To this mixture, dryDMF (100 mL) was added and the resulting mixture was stirred in the dark for 20 h. The reaction was quenched with methanol and concentrated in vacuo. The residue was diluted with 150 mL of DCM and washed with water (200 mL), saturated aqueous sodium sulfite (200 mL), and brine (100 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash columnchromatography on silica gel (50percent ethyl acetate / hexanes) to afford the desired product (3.1 g, 95percent yield) as a white solid. ESI-MS m/z: 279.5 [M + H].
90% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 18 h; Darkness To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine 41a (7.19 g, 46.8 mmol) in 70 mL of DMF was added N-iodosuccinimide (11.06 g, 49.2 mmol). The solution was stirred in the dark for 18 h at rt before being poured into 100 mL of H2O. The resulting tan precipitate was collected by suction filtration and dried under high vacuum to afford iodide 41b (11.8 g, 90percent) as a tan solid.
86.9% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; Example 1; Preparation of 2-(2'-methyl-β-D-ribofuanosyl)-2,6-dihydro-2,3,5,6-tetraaza-benzo[cd]azulen-7-one (Compound 301); Step 1; 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The yellow residue was suspended in hot 10percent solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6percent) of the title compound as off-white crystals. The mother liquid was evaporated up to volume and crystallized again from ethanol to give 2.47 g (12.3percent) of the target product. The total yield is close to 100percent; Tm 212-214° C. (dec); UV λmax: 307, 266, 230, 227 nm (methanol); MS: 277.93 (M-H), 313 (M+Cl); 1H-NMR (DMSO-d6): 12.94 (s, 1H, NH), 8.58 (s, 1H, H-2), 7.94 (s, 1H, H-8).
86% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; To a solution of 4-chloro-7H-pyrrolo[2, 3-D]pyrimidine1 (39 mmol) in DMF (50 ml_) was added in several portions /V-iodosuccinimide (8.8 g). After stirring overnight at 200C, EtOAc (500 ml) was added and the solution was washed three times with water (150 ml). The organic layer was filtered through a short silica column and concentrated in vacuo. Yield: 86percent (9.3 g); MS: 279 1' Available from Toronto Research Chemicals
85.8% at 20℃; for 3 h; A mixture of 249 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (500 g, 3255.84 mmol) and 250 NIS (805.74 g, 3581.43 mmol) in 21 DMF (3.3 L) was stirred at rt for 3 hrs. The mixture was poured into ice water (20 L) and resulting solid was filtered, washed with saturated sodium thiosulphate solution (4×2.5 L), water (4×2.5 L) and dried under vacuum to afford the 237 title compound as an off white solid (780 g, 85.8percent). 1HNMR (400 MHz, DMSO-d6): 7.94 (s, 1H), 8.59 (s, 1H). LCMS m/z=279.6 [MH]+
85% With N-iodo-succinimide In N,N-dimethyl-formamide at 22℃; for 2.5 h; Inert atmosphere N,N-Dimethylformamide (DMF) (47mL) was added to a mixture of 56 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (4.60g, 29.8mmol) and 57 N-iodosuccinimide (6.82g, 30.3mmol) under a nitrogen atmosphere. The solution was stirred at 22°C for 2.5h before the mixture was poured into ice water (150mL). The precipitate was filtered, washed with water and n-pentane and dried to give 7.05g (25.2mmol, 85percent) of 12 1 as a pale brown powder; mp. 187–188°C (dec.) (lit [39]. 196–199°C), Rf=0.16 (n-pentane/EtOAc, 10/1). 1H NMR (400MHz, DMSO‑d6): 12.94 (br s, 1H), 8.59 (s, 1H), 7.94 (d, J=2.5, 1H). The spectroscopic data corresponded well with that reported previously [39].
85% With N-iodo-succinimide In dichloromethane for 2 h; Heating / reflux Scheme 1General Synthesis of 5-Aryl pyπOlor2,3-d1pyrimidine CompoundsP X,Y = H1F , CI.C F31C N. CH3, OCH3, NH2, N(CH3J2, OCF31S F5X,Y = H, F, Cl, CF3,C N, CH3, OCH31N H2, N(CH3)2,O CF3,S F5EXAMPLE 27 4-CHLORO-5-IODO-7-BENZENESULFONYL-7H-PYRROLO[2,3-D]PYRIMIDINE1H-NMR (CD3ODMOO MHz): 8.75 (s, IH), 8.22 (dm, J = 6.5 Hz, 2H), 7.94 (s, IH), 7.68 (tm, J = 8.6 Hz, IH), 7.55 (tm, J = 8.6 Hz, 2H). MS (ES+, m/z): 419.9 (M++l, 100.0).
83% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; Preparation 109; 4-Chloro-5-iodo-7H-pyrrolo|"2.3-2SO3. Wash the organic fraction with 10 percent Na2SO3 (2x100 mL), saturate aqueous sodium chloride solution (150 mL), dry over Na2SO4 and evaporate. Crystalize the yellow residue from ethanol to yield 16.2 g (83percent) of 4-chloro-5-iodo-7H-pyrrolo[2,3-
82% With N-iodo-succinimide In chloroform for 1 h; Heating / reflux METHOD P
4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine
To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (30 g/0.02 mol) dissolved in 80 mL of chloroform was added 4.5 grams (0.02 mol) of N-iodosuccinimide and the resulting mixture heated at reflux for 1 hour.
After cooling to room temperature, the percipitate was removed by filtration and dried under reduced pressure affording 4.6 grams (82percent) of the title compound.
82% With N-iodo-succinimide In dichloromethane at 20℃; for 1 h; To a vigorously stirred solution of 11 (1.0 g; 6.51 itimol) in CH2Cl2 (55 itiL) was added 95percent N-iodosuccimide (1.70 g; 7.18 mmol) . The reaction mixture was stirred at room temperature for 1 h, during which time more precipitate appeared. The solid was filtered and recrystallized in hot methanol to afford 12 as slightly grey crystals (1.49 g; 82percent yield): 1H NMR (400 MHz, DMSO-d6) δ 12.96 (s br, IH, NH), 8.59 (s, IH, 2-H) , 7.94 (s, IH, 6-H) ; 13C NMR (100 MHz, DMSO-d6) δ 151.2, 150.4, 150.2, 133.6, 115.5, 51.7; HRMS (FAB+) calcd for C6H4N3ClI (M+H+) : 279.9139, found: 279.9141.
82% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 3 h; Inert atmosphere Take a 250 mL two-necked flask, add compound 5 (5 g, 33 mmol), argon,Anhydrous DMF solution was added slowly and NIS (8.1 g, 36 mmol, 1.1 equiv.) In anhydrous DMF was added slowly and stirred at room temperature for 3 h. Add saturated sodium thiosulfate solution(50 mL). The EA (100 mL) was added, the organic phase was collected, washed with saturated brine, extracted, dried over anhydrous sodium sulfate, (PE: EA = 4: 1) to give 7.4 g of product as a white solid in 82percent yield.
77% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 10 h; (e)
5 g (32.56 mmol) of 4-chloropyrrolo[2,3-d]pyrimidine and 11 g (50 mmol) of N-iodosuccinimide are dissolved in 60 ml of DMF, and the mixture is stirred at RT for 10 hours.
The mixture is worked up using aqueous sodium thiosulfate solution and extracted with ether.
The organic phase is washed with aqueous sodium thiosulfate solution and ammonium chloride solution.
The solid which finally remains behind is recrystallized from methanol, giving 7 g (77percent) of 4-chloro-5-iodopyrrolo[2,3-d]pyrimidine in the form of a pale-brownish solid which melts at 195-196° C.
74.6% With N-iodo-succinimide In DMF (N,N-dimethyl-formamide) at 20℃; 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 ml of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The yellow residue was suspended in hot 10percent solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6percent) of the title compound as off-white crystals. The mother liquid was evaporated up to volume and crystallized again from ethanol to give 2.47 g (12.3percent) of the title product. The total yield is close to 100percent. Tm 212-214 (dec). UV λmax: 307, 266, 230, 227 nm (methanol). MS: 277.93 (M-H), 313 (M+Cl). 1H-NMR (DMSO-d6): 12.94 (s, 1H, NH), 8.58 (s, 1H, H-2), 7.94 (s, 1H, H-8).
74% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 2 h; Compound 13a (5.0 g, 32.56 mmol, 1.00 equiv) was taken up in DMF 60 mL. and to the resulting solution was added N-iodosuccinimide (7.3 g, 32.45 mmol, 1.00 equiv) in portions at room temperature. The resulting reaction was allowed to stir for 2 hours at room temperature, and then was concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel and eluted with ethyl acetate/petroleum ether (1:3) to provide 6.7 g (74percent) of compound 13b as a white solid.
72% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; Darkness Step 1: 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine A mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 20 mmol) and NIS (4.9 g, 20.1 mmol) in DMF (100 mL) was stirred in darkness at room temperature overnight. Then the mixture was concentrated in vacuo. The residue was treated with 10percent Na2SO3 and filtered to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (4.0 g, yield 72percent) as a yellow solid.
52% With N-iodo-succinimide In dichloromethane at 20℃; for 2 h; Darkness Synthesis of 7-(2-nitrobenzyloxy)methyl-7-deaza-2′-deoxyadenosine-5′-triphosphate
6-Chloro-7-iodo-7-deazapurine (dA.23): Compound dA.23 was synthesized according to the procedure described by Ju et al. (2006, which is incorporated herein by reference). To a suspension of 6-chloro-7-deazapurine (1.00 g, 6.51 mmol) in anhydrous CH2Cl2 (55 mL) was added N-iodosuccinimide (1.70 g, 7.56 mmol). The reaction was protected from light while stirring at room temperature for two hours. The reaction was then concentrated down in vacuo. The material was re-crystallized from hot methanol to yield 6-chloro-7-iodo-7-deazapurine dA.23 (0.94 g, 52percent).
13.57 g With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 1 h; Step 1
Synthesis of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine
N-Iodosuccinimide (11.6 g) was added to a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (7.52 g) in DMF (49 ml) at room temperature.
The mixture was stirred at the same temperature for 1 hour, and water (150 ml) was added to the reaction mixture.
The resulting precipitate was collected by filtration, washed with water, and dried to obtain the title compound as a light-yellow solid (13.57 g).
ESI-MS m/z 280, 282 (MH+).
2.8 g With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 1 h; 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (2 g, 13.02 mmol) was charged in DCM (60 mL) and was added N-iodosuccinimide (3.80g, 16.92 mmol). To this reaction mixture was added DMF (6 mL) and the reaction mixture was stuffed at RT for 1 h. The progress of reaction was monitored by TLC and NMR. After completion of reaction, the solid obtained was filtered off and washed with pentane (30 mL). The solid obtained was dried under vacuum to get 4-chloro-5-iodo-7H-pyrrolo [2, 3-d] pyrimidine (2.8 g).

Reference: [1] Patent: US2005/107312, 2005, A1,
[2] Patent: US2005/215510, 2005, A1,
[3] Patent: US2005/215511, 2005, A1,
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  • 3
  • [ 516-12-1 ]
  • [ 3680-69-1 ]
  • [ 123148-78-7 ]
YieldReaction ConditionsOperation in experiment
86.9% at 20℃; Step 1:4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The yellow residue was suspended in hot 10percent solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6percent) of the title compound as off-white crystals. The mother liquid was evaporated up to volume and crystallized again from ethanol to give 2.47 g (12.3percent) of the target compound. The total yield is close to 100percent;Tm 212-214° C. (dec);UV λmax: 307, 266, 230, 227 nm (methanol);MS: 277.93 (M-H), 313 (M+Cl);1H-NMR (DMSO-d6): 12.94 (s, 1H, NH), 8.58 (s, 1H), 7.94 (s, 1H).
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