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[ CAS No. 7390-62-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 7390-62-7
Chemical Structure| 7390-62-7
Chemical Structure| 7390-62-7
Structure of 7390-62-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7390-62-7 ]

CAS No. :7390-62-7 MDL No. :MFCD00127786
Formula : C5H5N5S Boiling Point : -
Linear Structure Formula :- InChI Key :BHVOFCPOXNYVCE-UHFFFAOYSA-N
M.W : 167.19 Pubchem ID :5354970
Synonyms :

Calculated chemistry of [ 7390-62-7 ]      Expand+

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 : 3.0
Molar Refractivity : 43.48
TPSA : 115.47 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.76
Log Po/w (XLOGP3) : -0.57
Log Po/w (WLOGP) : 0.61
Log Po/w (MLOGP) : -0.9
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 0.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.12
Solubility : 12.6 mg/ml ; 0.0753 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 6.9 mg/ml ; 0.0412 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.91
Solubility : 2.06 mg/ml ; 0.0123 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 7390-62-7 ]

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 [ 7390-62-7 ]

* 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.

  • Downstream synthetic route of [ 7390-62-7 ]

[ 7390-62-7 ] Synthesis Path-Downstream   1~97

  • 1
  • [ 118-70-7 ]
  • [ 17356-08-0 ]
  • [ 7390-62-7 ]
YieldReaction ConditionsOperation in experiment
54.9% In 1,2-dichloro-benzene; at 160℃; for 14h; Step 1b. 6-Amino-7H-purine-8(9H)-thione (Compound 104); A mixture of 4,5,6-triaminopyfimidine sulfate (50.0 g, 223.0 mmol), NaOH (19.7 g, 493.0 mmol) and water (500 mL) was heated to 80 C. until all the solids dissolved. The solution was cooled to 05 C. and the pH was adjusted to 7.0 with 1N HCl, whereupon the free base crystallized as white needles (27.6 g, 99%). A mixture of <strong>[118-70-7]4,5,6-triaminopyrimidine</strong> 103 (10.0 g, 80.0 mmol), thiourea (18.3 g, 240.0 mmol) in 1,2-dichlorobenzene (60 mL) was stirred for 14 hours at 160 C. Cooled to room temperature and the mixture solidified. Poured out the clear liquid, the solid was triturate and was diluted with brine. The mixture was stirred for 2 hours at room temperature and filtered to obtain crude product. The crude product was washed with brine and ether, dried to give title compound 104 as a light yellow solid (7.35 g, 54.9%). 1H NMR (DMSO-d6) delta 6.77 (s, 2H), 8.08 (s, 1H), 12.06 (s, 1H), 13.05 (s, 1H).
  • 2
  • [ 50625-94-0 ]
  • [ 7390-62-7 ]
  • 4-[3-(6-Amino-9H-purin-8-ylsulfanyl)-2-hydroxy-propoxy]-benzoic acid ethyl ester [ No CAS ]
  • 4
  • [ 7390-62-7 ]
  • [ 65291-30-7 ]
  • 8-[(S)-2-hydroxy-3-(trityloxy)propyl]sulfanyl}adenine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;
  • 5
  • [ 7390-62-7 ]
  • [ 129940-50-7 ]
  • [ 303014-70-2 ]
  • [ 303014-71-3 ]
  • 3-[(S)-2-hydroxy-3-(trityloxy)propyl]-8-[(R)-2-hydroxy-3-(trityloxy)propyl]sulfanyl}adenine [ No CAS ]
  • 6
  • [ 4214-28-2 ]
  • [ 7390-62-7 ]
  • 8-(2,4-dimethyl-phenylsulfanyl)adenine [ No CAS ]
  • 7
  • [ 637-87-6 ]
  • [ 7390-62-7 ]
  • 8-(4-chloro-phenylsulfanyl)adenine [ No CAS ]
  • 8
  • [ 766-85-8 ]
  • [ 7390-62-7 ]
  • [ 696574-58-0 ]
  • 9
  • [ 529-28-2 ]
  • [ 7390-62-7 ]
  • 8-(2-methoxy-phenylsulfanyl)adenine [ No CAS ]
  • 10
  • [ 672-57-1 ]
  • [ 7390-62-7 ]
  • 8-[2-chloro-5-(trifluoromethyl)phenylsulfanyl]adenine [ No CAS ]
  • 11
  • [ 615-41-8 ]
  • [ 7390-62-7 ]
  • 8-(2-chloro-phenylsulfanyl)adenine [ No CAS ]
  • 12
  • [ 696-62-8 ]
  • [ 7390-62-7 ]
  • 8-(4-methoxy-phenylsulfanyl)adenine [ No CAS ]
  • 13
  • [ 20469-63-0 ]
  • [ 7390-62-7 ]
  • 8-(2,4-dimethoxy-phenylsulfanyl)adenine [ No CAS ]
  • 14
  • [ 22445-41-6 ]
  • [ 7390-62-7 ]
  • 8-(3,5-dimethyl-phenylsulfanyl)adenine [ No CAS ]
  • 15
  • [ 5159-41-1 ]
  • [ 7390-62-7 ]
  • 8-[2-(hydroxymethyl)phenylsulfanyl]adenine [ No CAS ]
  • 16
  • [ 13329-40-3 ]
  • [ 7390-62-7 ]
  • 8-(4-acetyl-phenylsulfanyl)adenine [ No CAS ]
  • 17
  • [ 1122-42-5 ]
  • [ 7390-62-7 ]
  • 8-(2,5-dimethyl-phenylsulfanyl)adenine [ No CAS ]
  • 18
  • [ 4897-68-1 ]
  • [ 7390-62-7 ]
  • 8-(2-bromo-5-methoxy-phenylsulfanyl)adenine [ No CAS ]
  • 19
  • [ 7145-82-6 ]
  • [ 7390-62-7 ]
  • 8-(2,4,5-trichloro-phenylsulfanyl)adenine [ No CAS ]
  • 20
  • [ 3032-81-3 ]
  • [ 7390-62-7 ]
  • 8-((3,5-dichlorophenyl)thio)-9H-purin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In N,N-dimethyl-formamide; at 110℃;Inert atmosphere; Sealed tube; 8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), 3,5-dichloro-iodobenzene (10.8 mmol), and anhydrous DMF (24 mL) were added to a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape and heated at 1 10 °C with stirring for 24-36 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5) to yield 15 as a yellow solid in 44 percent yield. -NMR (400 MHz, DMSO-i/6) delta 13.49 (IH, br s), 8.13 (IH, s), 7.59 (IH, s), 7.47 (2H, s), 7.36 (2H, br s); MS (ESI): m/z 312.1 [M + H+].
  • 21
  • [ 29898-32-6 ]
  • [ 7390-62-7 ]
  • 8-((2,4-dichlorophenyl)thio)-9H-purin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In N,N-dimethyl-formamide; at 110℃; for 24.0h;Inert atmosphere; Sealed tube; 8-Mercaptoadenine (1, 1.23 g, 7 mmol), 1 -iodo-2,4-dichlorobenzene (3 g, 1 1 mmol), neocuprine hydrate (0.3 g, 1.4 mmol), Cul (0.28 g, 1.4 mmol), NaO/-Bu (1.4 g, 14 mmol) and DMF (20 mL) were charged in a nitrogen protected dry vessel. The reaction vessel was sealed and placed in an oil bath (1 10 C) and stirred for 24 hrs. The reaction mixture was then cooled to room temperature and DMF was removed in vacuo. The crude material was purified by silica gel flash chromatography (CH2Cl2:CH3OH:CH3COOH, 60: 1 :0.5 to 20: 1 :0.5) to afford the 2.0 g (87 %) of 18. MS (ESI): m/z 312.0 [M + H]+.
  • 22
  • [ 29682-41-5 ]
  • [ 7390-62-7 ]
  • 8-(2,5-dichloro-phenylsulfanyl)-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 23
  • [ 94670-76-5 ]
  • [ 7390-62-7 ]
  • [ 852030-25-2 ]
YieldReaction ConditionsOperation in experiment
97% With sodium t-butanolate;copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; In N,N-dimethyl-formamide; at 110℃; for 24.0h; 8-Mercaptoadenine (602 mg, 3.6 mmol), neocuproine hydrate (81 mg, 0.36 mmol), CuI (69 mg, 0.36 mmol), NaO-t-Bu (692 mg, 7.2 mmol), 5-bromo-6-iodo~benzo[l,3]dioxole (3.53 g, 10.8 mmol) and anhydrous DMF (24 mL) were charged in a nitrogen box. The vessel was sealed with Teflon tape, placed in an oil bath (1100C) and magnetically stirred for 24 h. The solvent was removed under high vacuum and the crude purified by column chromatography on silica gel EPO <DP n="32"/>(EtOAc:CH2C12:MeOH at 2:2:1) to provide the product (1.29 g, 97%). IH NMR (400 MHz, acetone-d6) 8.07 (s, IH), 7.28 (s, IH), 7.15 (s, IH), 7.08 (bs, 2H), 6.13 (s, 2H); MS m/z 366.0 (M+H)+.
  • 24
  • [ 92636-36-7 ]
  • [ 7390-62-7 ]
  • 8-((4-(1H-pyrrol-1-yl)phenyl)thio)-9H-purin-6-amine [ No CAS ]
  • 25
  • [ 175278-00-9 ]
  • [ 7390-62-7 ]
  • 8-(2-trifluoromethoxy-phenylsulfanyl)adenine [ No CAS ]
  • 26
  • [ 556-52-5 ]
  • [ 7390-62-7 ]
  • 2-amino-8-(2,3-dihydroxypropylthio)purine [ No CAS ]
  • 29
  • [ 7390-62-7 ]
  • 8-(6-bromo-3,4-methylenedioxyphenylthio)-9-(pent-4-ynyl)adenine [ No CAS ]
  • 31
  • [ 7390-62-7 ]
  • [ 905449-68-5 ]
  • 32
  • [ 7390-62-7 ]
  • 8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(pent-4-ynyl)adenine [ No CAS ]
  • 33
  • [ 7390-62-7 ]
  • 8-(6-bromo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine [ No CAS ]
  • 34
  • [ 7390-62-7 ]
  • 8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine [ No CAS ]
  • 35
  • [ 7390-62-7 ]
  • [ 873437-14-0 ]
  • 36
  • [ 7390-62-7 ]
  • 8-(2,5-dimethyl-phenylsulfanyl)-9-pent-4-ynyl-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 37
  • [ 7390-62-7 ]
  • 8-((2,4-dichlorophenyl)thio)-9-(pent-4-yn-1-yl)-9H-purin-6-amine [ No CAS ]
  • 38
  • [ 7390-62-7 ]
  • 8-(2,5-dichloro-phenylsulfanyl)-9-pent-4-ynyl-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 39
  • [ 7390-62-7 ]
  • 8-(3,5-dichloro-phenylsulfanyl)-9-pent-4-ynyl-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 40
  • [ 7390-62-7 ]
  • 1-[4-(6-amino-9-pent-4-ynyl-9<i>H</i>-purin-8-ylsulfanyl)-phenyl]-ethanone [ No CAS ]
  • 41
  • [ 7390-62-7 ]
  • 8-(4-(1H-pyrrol-1-yl)phenylthio)-9-(pent-4-ynyl)-9H-purin-6-amine [ No CAS ]
  • 42
  • [ 7390-62-7 ]
  • 8-(2-bromo-5-methoxy-phenylsulfanyl)-9-pent-4-ynyl-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 43
  • [ 7390-62-7 ]
  • 9-pent-4-ynyl-8-(2-trifluoromethoxy-phenylsulfanyl)-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 44
  • [ 7390-62-7 ]
  • 9-(pent-4-ynyl)-8-(2,4,5-trichloro-phenylsulfanyl)adenine [ No CAS ]
  • 45
  • isobutyl p-(3-bromo-2-oxo)-propyloxy benzoate [ No CAS ]
  • [ 7390-62-7 ]
  • 8-[3-[(p-isobutylcarbonyl)-phenoxy]-2-oxo-propylthio]-adenine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% EXAMPLE 30 8-[3-[(p-isobutylcarbonyl)-phenoxy]-2-oxo-propylthio]-adenine From 8-mercapto-adenine and isobutyl p-(3-bromo-2-oxo)-propyloxybenzoate. Yield 80%, m.p. 184 C.
  • 46
  • [ 147539-08-0 ]
  • [ 7390-62-7 ]
  • [ 147538-99-6 ]
YieldReaction ConditionsOperation in experiment
75% EXAMPLE 36 8-[3-[(p-carboxy)-phenoxy]-2-oxo-propylthio]-adenine From 8-mercapto-adenine and p-(2-oxo,3-bromo propyloxy)-benzoic acid. Yield 75%, m.p.196-198 C.
75% EXAMPLE 36 8-[3-[(p-carboxy)-phenoxy]-2-oxo-propylthio]-adenine From 8-mercapto-adenine and p-(2-oxo,3-bromo propyloxy)-benzoic acid. Yield 75%, m.p.196-198oC.
  • 47
  • [ 50625-94-0 ]
  • [ 7390-62-7 ]
  • [ 104343-40-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In N-methyl-acetamide; ethanol; ethyl acetate; EXAMPLE 2 6-amino-8-[[3-(4-ethoxycarbonyl)phenoxy-2-hydroxy]propyl]-thio}purine A mixture of 8-mercapto-adenine (5 g, 30 mmoles), 1-(4-ethoxycarbonyl)phenoxy-2,3-epoxypropane (10 g, 45 mmoles), dimethylformamide (100 ml) and pyridine (20 ml) is heated to 30-40 C. under stirring for 24 hours, the cloudy solution is then filtered on celite, washed with ethanol and concentrated to dryness under vacuum. The residue is dissolved in ethanol and poured onto silica gel (150 g). The solvent is evaporated off and the residue is taken up in ethyl acetate (300 ml) and heated at reflux temperature. The reaction mixture is then allowed to cool and filtered and the solid on filter is treated as above once again. The residue is then crystallized from ethanol (350 ml) and ethyl acetate (100 ml) yielding 4.6 g of the compound of the title with m.p. 200-201 C. By concentrating to dryness the filtrate, further 0.99 g of the compound of the title (m.p. 200-1 C.) crystallize out.
  • 48
  • isobutyl p-(3-bromo-2-oxo)-propyloxy benzoate [ No CAS ]
  • [ 7390-62-7 ]
  • [ 147538-93-0 ]
YieldReaction ConditionsOperation in experiment
80% EXAMPLE 30 8-[3-[(p-isobutyloxycarbonyl)-phenoxy]-2-oxo-propylthio]-adenine From 8-mercapto-adenine and isobutyl p-(3-bromo-2-oxo)-propyloxybenzoate. Yield 80%, m.p.184oC.
  • 49
  • [ 455-13-0 ]
  • [ 7390-62-7 ]
  • [ 1102466-36-3 ]
YieldReaction ConditionsOperation in experiment
83% With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate; In N,N-dimethyl-formamide; at 120℃; for 20.0h; A mixture of 400 mg (2.4 mmol) of 6-amino-9H-purine-8-thiol (cf. Llauger et al., "Evaluation of 8-Arylsulfanyl, 8-Arylsulfoxyl, and 8-Arylsulfonyl Adenine Derivatives as Inhibitors of the Heat Shock Protein 90", J. Med. Chem., 2005, vol. 48, p. 2892), 50 mg (0.24 mmol) of neocuproine, 46 mg (0.24 mmol) of CuI and 584 mg (4.8 mmol) of potassium te/t-butoxide was suspended in 10 ml_ of anhydrous DMF. Over the white suspension, 1.95 g (7.2 mmol) of 4- iodobenzothfluoride, dissolved in 7 ml_ anhydrous DMF, were also added. The crude was stirred for 2Oh at 12O0C. Removal of the solvent under high vacuum afforded a dark brown residue that was purified by flash chromatography (CH2CI2/EtOAc/MeOH, 2:2:0.5) to give 620 mg, (1.99 mmol, 83%) of 8-(4- (thfluoromethyl)phenylthio)-9H-purin-6-amine as a pale brown solid. 1H-NMR[CDCIs/CDsOD, δ, ppm]: 8.12 (s, 1 H), 7.54 (d, J=8.5 Hz, 2H), 7.54 (d, J=8.5 Hz, 2H).
  • 50
  • [ 7390-62-7 ]
  • [ 3034-48-8 ]
  • [ 1147011-89-9 ]
  • 51
  • [ 59820-92-7 ]
  • [ 7390-62-7 ]
  • [ 1156467-97-8 ]
YieldReaction ConditionsOperation in experiment
23% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 18.0h; Intermediate 11 : 8-[(7-Nitro-2,3-dihydro-l ,4-benzodioxin-6-yl)thio]-9H-purin-6-amine; A mixture of 6-amino-9H-purine-8-thiol (0.250 g, 1.50 mmol), 6-bromo-7- nitro-2,3-dihydro-benzo[l ,4]dioxine (0.390 g, 1.50 mmol) and K2CO3 (0.207 g, 1.50 mmol) in DMF (5 mL) heated 100 0C for 18 h. The reaction mixture was cooled and evaporated under reduced pressure, the crude obtained was chromatagraphed over SiO2 using gradient of 0-20% methanol in dichloromethane to give product 8-(7-nitro-2,3- dihydro-benzo[l ,4]dioxin-6-ylsulfanyl)-9H-purin-6-ylamine as yellow solid (0.120 g, 23%); LC-MS [M+H]+ 347.0.
  • 52
  • [ 81634-45-9 ]
  • [ 7390-62-7 ]
  • [ 1245751-01-2 ]
  • 53
  • [ 128334-28-1 ]
  • [ 7390-62-7 ]
  • [ 1245751-02-3 ]
  • 54
  • [ 101911-11-9 ]
  • [ 7390-62-7 ]
  • [ 1245751-03-4 ]
  • 55
  • [ 7390-62-7 ]
  • [ 57744-67-9 ]
  • [ 1289544-98-4 ]
YieldReaction ConditionsOperation in experiment
With sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 24h; 8- (7-Iodo-2,3-dihydrobenzo[b| [l,4]dioxin-6-ylthio)-9H-purin-6-amine (S9-3).; To a solution of S9-2 (1.26 g, 4.8 mmol) in DMF (15 mL) was added 8-mercaptoadenine (0.400 g, 2.4 mmol), neocuproine (0.056 g, 0.24 mmol), Cul (0.044 g, 0.24 mmol) and NatOBu (0.460 g, 4.8 mmol). The reaction mixture was stirred at 110 °C for 24h. Solids were filtered and the filtrate was condensed under reduced pressure. The residue was flash chromatographed (CHCl3:MeOH:AcOH, 60:0.5:0.5 to 30:0.5:0.5) to yield 0.578 g (80%) of intermediate coupling product (MS (ESI) m/z 301.9 [M+H]+). To 0.400 g (1.4 mmol) of this and NIS (0.945 g, 4.2 mmol) in acetonitrile (15 mL) was added TFA (540 μ, 0.800 g, 7 mmol) and the mixture Was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography(CHCl3:MeOH:AcOH, 60:0.5:0.5 to 30:0.5:0.5) to give S9-3 (0.436 g, 73%). 1H NMR (DMSO-de, 500 MHz) δ 8.37 (s, 1H), 8.03 (br s, 2H), 7.47 (s, 1H), 7.10 (s, 1H), 4.25-4.27 (m, 4H); MS (ESI) m/z 427.9 [M+H]+.
  • 56
  • [ 7390-62-7 ]
  • [ 116632-14-5 ]
  • [ 1289544-46-2 ]
YieldReaction ConditionsOperation in experiment
37% With sodium t-butanolate;copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; In N,N-dimethyl-formamide; at 115℃; for 20h; 8-(3-aminonaphthalen-2-ylthio)-9H-purin-6-amine (S13-4).; A mixture of 8- mercaptoadenine (20.7 mg, 0.124 mmol), neocuproine hydrate (3.9 mg, 0.0185 mmol), Cul (3.5 mg, 0.0185 mmol), sodium tert-butoxide (23.7 mg, 0.24 mmol), S13-3 (100 mg, 0.37 . mmol) and DMF (2 mL) were heated at 115C for 20 h. The solvent was removed under reduced pressure and the residue was purified by preparatory TLC (CH2Cl2:MeOH-NH3 (7N), 10:1) to give 14 mg (37%) of S13-4 as a solid. 1H NMR (500 MHz, CDC^/MeOH-cU) delta 8.18 (s, 1H), 8.12 (s, 1H), 7.71 (d, J= 8.3 Hz, 1H), 7.62 (d, J= 8.1 Hz, 1H), 7.40-7.46 (m, 1H), 7.24-7.30 (m, 1H), 7.20 (s, 1H); MS (ESI) m/z 308.95 [M+H]+.
  • 57
  • [ 98591-57-2 ]
  • [ 7390-62-7 ]
  • [ 1360066-65-4 ]
  • 58
  • [ 1262411-89-1 ]
  • [ 7390-62-7 ]
  • [ 1289544-14-4 ]
YieldReaction ConditionsOperation in experiment
44% With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80℃; for 48.0h;Inert atmosphere; 8-(2,3-Dihydrobenzomran-6-yltHo)-9iT-purin-6-arriine (S2-3):To a solution of S2-2 (50 mg, 0.2 mmol) in DMF (2 mL) was added <strong>[7390-62-7]8-mercaptoadenine</strong> (34 mg, 0.2 mmol), Cs2C03 (99.4 mg, 0.3 mmol) and PdCl2(dppf) (33 mg, 0.02 mmol). The mixture was degassed for 5 minutes with argon and stirred at 80C under argon protection for 48 h. The resulting mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (CH2Cl2:MeOH, 100:0 to 90:10) to provide S2-3 (25 mg, 44% yield) as a yellow solid.¾ MR (500 MHz, CD3OD, δ): 8.14 (s, 1H), 7.24 (d, J= 7.6 Hz, 1H), 7.07 (d, J= 7.3 Hz, 1H), 6.97 (s, 1H), 4.62 (t, J= 8.7 Hz, 2H), 3.25 (t, J= 8.7 Hz, 2H).MS (ESI): mh= 285.8 [M+H]+.HRMS (ESI) m/z [M+H]+ calc'd. for C13Hi2N5OS = 286.0763; found 286.0768.
  • 59
  • [ 1289544-19-9 ]
  • [ 7390-62-7 ]
  • [ 1289544-20-2 ]
  • 60
  • [ 944280-06-2 ]
  • [ 7390-62-7 ]
  • [ 1289544-50-8 ]
YieldReaction ConditionsOperation in experiment
47% With copper(l) iodide; tetrabutylammomium bromide; sodium t-butanolate; In N,N-dimethyl-formamide; at 190℃; for 1.0h;microwave irradiation; 8-((6-Amino-2,3-dihydro-lii-inden-5-yl)thio)-9-if-purin-6-amine (S-5):The mixture of <strong>[7390-62-7]8-mercaptoadenine</strong> (64 mg, 0.38 mmol), S-4 (100 mg, 0.38 mmol), Cul (14.7 mg, 0.07 mmol), sodium t-butoxide (111 mg, 1.15 mmol) and tetrabutylammonium bromide (24.9 mg, 0.07 mmol) in anhydrous DMF (4 mL) was vortexed and heated at 190C under microwave for lh. The resulting mixture was condensed and purified by flash chromatography (methylene chloride/methanol, gradient 0% to 10%) to provide S-5 (54 mg, 47% yield) as a while solid.'H NMR (500 MHz, MeOH-^/CDCf,, δ): 8.11 (s, 1H), 7.36 (s, 1H), 6.81 (s, 1H), 2.85 (m, 4H), 2.06 (m, 2H).MS (ESI): m/z = 299.02 [M+H]+.
  • 61
  • [ 1289544-45-1 ]
  • [ 7390-62-7 ]
  • [ 1289555-27-6 ]
  • 62
  • [ 1360066-75-6 ]
  • [ 7390-62-7 ]
  • [ 1360066-64-3 ]
  • 63
  • [ 1360066-76-7 ]
  • [ 7390-62-7 ]
  • [ 1360066-66-5 ]
  • 64
  • [ 175278-30-5 ]
  • [ 7390-62-7 ]
  • [ 1360066-70-1 ]
YieldReaction ConditionsOperation in experiment
49% With copper(l) iodide; tetrabutylammomium bromide; sodium t-butanolate; In N,N-dimethyl-formamide; at 150℃; for 1.5h;Sealed tube; Microwave irradiation; General procedure: In a conical-bottomed microwave vial, the mixture of 8 mercaptoadenine (0.1 mmol), respective aryl iodide (0.1 mmol), Cul (0.02 mmol), NaO?-Bu (0.3 mmol) and ?-butyl ammonium bromide (0.02 mmol) in DMF (2 mL) was charged. The sealed vial was irradiated in the microwave for 1.5 h at 150 °C. After cooling, the reaction mixture was condensed under reduced pressure and purified by flash chromatography (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). [0216] 8-((4-Bromo-2-ethylphenyl)thio)-9H-purin-6-amine (2a). Obtained by method B as a light yellow solid in 49 percent yield. MS (ESI): m/z 351.8 [M + H]+.
  • 65
  • [ 90-14-2 ]
  • [ 7390-62-7 ]
  • [ 1360066-67-6 ]
  • 66
  • [ 609-73-4 ]
  • [ 7390-62-7 ]
  • [ 1360066-71-2 ]
  • 67
  • [ 223463-13-6 ]
  • [ 7390-62-7 ]
  • [ 1360066-68-7 ]
  • 68
  • [ 13101-40-1 ]
  • [ 7390-62-7 ]
  • [ 1360066-72-3 ]
  • 69
  • [ 19752-57-9 ]
  • [ 7390-62-7 ]
  • [ 1360066-73-4 ]
  • 70
  • [ 149428-64-8 ]
  • [ 7390-62-7 ]
  • [ 1360066-74-5 ]
  • 71
  • [ 31928-47-9 ]
  • [ 7390-62-7 ]
  • [ 1360066-69-8 ]
  • 72
  • [ 115666-43-8 ]
  • [ 7390-62-7 ]
  • [ 1360066-63-2 ]
  • 73
  • [ 5279-32-3 ]
  • [ 7390-62-7 ]
  • [ 852030-25-2 ]
  • 74
  • [ 25812-80-0 ]
  • [ 7390-62-7 ]
  • [ 958026-16-9 ]
  • 75
  • [ 1289167-38-9 ]
  • [ 7390-62-7 ]
  • [ 1156468-12-0 ]
  • 76
  • [ 1289167-38-9 ]
  • [ 7390-62-7 ]
  • [ 1156466-02-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: N,N,N′,N′-tetramethyl-N″-tert-butylguanidine / N,N-dimethyl-formamide / 10 h / 80 °C
  • 77
  • [ 6120-26-9 ]
  • [ 7390-62-7 ]
  • [ 958026-14-7 ]
  • 79
  • [ 75-15-0 ]
  • [ 49721-45-1 ]
  • [ 7390-62-7 ]
  • 80
  • [ 845866-78-6 ]
  • [ 7390-62-7 ]
  • 8-((3-bromo-5-(trifluoromethoxy)phenyl)thio)-9H-purin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In N,N-dimethyl-formamide; at 100.0℃;Inert atmosphere; Sealed tube; General procedure: 8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), respective aryl iodide (10.8 mmol), and anhydrous DMF (24 mL) were taken in a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape, heated at 1 10 C, and magnetically stirred for 24-36 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). [0223] 8-((3-Bromo-5-(trifluoromethoxy)phenyl)thio)-9H-purin-6-amine (2h). Obtained by method A as a light yellow solid in 41 % yield. MS (ESI): m/z 407.8 [M + H]+.
  • 81
  • 1-chloro-3,5-diiodobenzene [ No CAS ]
  • [ 7390-62-7 ]
  • 8-((3-chloro-5-iodophenyl)thio)-9H-purin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In N,N-dimethyl-formamide; at 110℃; for 24.0h;Inert atmosphere; Sealed tube; 8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), l-chloro-3,5- diiodobenzene (10.8 mmol), and anhydrous DMF (24 mL) were taken in a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape, heated at 1 10 C, and magnetically stirred for 24 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). Obtained as a light yellow solid in 67 % yield. MS (ESI): m/z 403.7 [M + H]+.
  • 82
  • [ 98027-84-0 ]
  • [ 7390-62-7 ]
  • 8-((2,6-dichloropyridin-4-yl)thio)-9H-purin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In N,N-dimethyl-formamide; at 110℃; for 24h;Inert atmosphere; Sealed tube; 8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), 2,6-dichloro-4- iodopyridine (10.8 mmol), and anhydrous DMF (24 mL) were taken in a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape, heated at 1 10 C, and magnetically stirred for 24 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). Obtained as a light yellow solid in 50 % yield. MS (ESI): m/z 312.8 [M + H]+.
  • 83
  • [ 5446-05-9 ]
  • [ 7390-62-7 ]
  • 8-((4-chloro-2-nitrophenyl)thio)-9H-purin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In N,N-dimethyl-formamide; at 110℃; for 18h;Inert atmosphere; Sealed tube; 8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), 4-chloro- l -iodo-2- nitrobenzene (10.8 mmol), and anhydrous DMF (24 mL) were taken in a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape, heated at 1 10 C, and magnetically stirred for 18 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). Obtained as a yellow solid in 85 % yield. MS (ESI): m/z 332.8 [M + H]+.
  • 84
  • [ 6797-79-1 ]
  • [ 7390-62-7 ]
  • 8-((4-chloro-2-fluorophenyl)thio)-9H-purin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In N,N-dimethyl-formamide; at 110℃; for 24.0h;Inert atmosphere; Sealed tube; General procedure: 8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-M3u (7.2 mmol), respective aryliodide (10.8 mmol), and anhydrous DMF (24 mL) were taken in a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape, heated at 1 10 C, and magnetically stirred for 24 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). [0467] 8-((4-chloro-2-fluorophenyl)thio)-9H-purin-6-amine (108 a). Obtained as a light yellow solid in 49 % yield. MS (ESI): m/z 296.1 [M + H]+.
  • 85
  • [ 175278-30-5 ]
  • [ 7390-62-7 ]
  • C18H18BrN5S [ No CAS ]
  • 8-((4-bromo-2-ethylphenyl)thio)-9-(pent-4-yn-1-yl)-9H-purin-6-amine [ No CAS ]
  • 86
  • [ 5876-51-7 ]
  • [ 7390-62-7 ]
  • 8-(benzo[1,3]dioxol-5-ylsulfanyl)adenine [ No CAS ]
  • 87
  • [ 29682-41-5 ]
  • [ 7390-62-7 ]
  • 8-(2,5-dichloro-phenylsulfanyl)-9-pent-4-ynyl-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 8-(2,5-dichlorophenylthio)-3-(pent-4-ynyl)-3H-purin-6-amine [ No CAS ]
  • 88
  • [ 672-57-1 ]
  • [ 7390-62-7 ]
  • 8-(2-chloro-5-trifluoromethyl-phenylsulfanyl)-9-pent-4-ynyl-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 8-(2-chloro-5-(trifluoromethyl)phenylthio)-3-(pent-4-ynyl)-3H-purin-6-amine [ No CAS ]
  • 89
  • [ 13101-40-1 ]
  • [ 7390-62-7 ]
  • 8-((3-bromo-5-chlorophenyl)thio)-9-(pent-4-yn-1-yl)-9H-purin-6-amine [ No CAS ]
  • 90
  • [ 20555-91-3 ]
  • [ 7390-62-7 ]
  • 8-((3,4-dichlorophenyl)thio)-9H-purin-6-amine [ No CAS ]
  • 91
  • [ 62720-28-9 ]
  • [ 7390-62-7 ]
  • 8-((2,3,4-trichlorophenyl)thio)-9H-purin-6-amine [ No CAS ]
  • 92
  • [ 6324-50-1 ]
  • [ 7390-62-7 ]
  • 8-(mesitylthio)-9H-purin-6-amine [ No CAS ]
  • 93
  • [ 6324-50-1 ]
  • [ 7390-62-7 ]
  • C19H21N5S [ No CAS ]
  • 8-(mesitylthio)-3-(pent-4-ynyl)-3H-purin-6-amine [ No CAS ]
  • 94
  • [ 175278-00-9 ]
  • [ 7390-62-7 ]
  • 9-pent-4-ynyl-8-(2-trifluoromethoxy-phenylsulfanyl)-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 3-(pent-4-ynyl)-8-(2-(trifluoromethoxy)phenylthio)-3H-purin-6-amine [ No CAS ]
  • 95
  • [ 75-15-0 ]
  • [ 118-70-7 ]
  • [ 7390-62-7 ]
YieldReaction ConditionsOperation in experiment
66% With potassium hydroxide; In ethanol; water;Reflux; To a mixture of compound 6 (4.13 g, 33 mmol) in solvents of EtOH (200 mL) and water (10 mL) was added KOH (2.28 g, 35 mmol) and CS2 (3.33 g, 43.8 mmol). The reaction mixture was stirred at reflux for overnight. The solvents were evaporated, and the residue were rinsed with water and acetone to obtain a yellow product 7 (3.64 g, 66%). Rf = 0.24 (1:9 MeOH/CH2Cl2), mp >350 C. 1H NMR (DMSO-d6): delta 6.59 (s, 2H, NH2), 7.98 (s, 1H, Ar-H), 12.20 (br s, 2H, 2 × NH). MS (ESI): 168 ([M+H]+, 90%); MS (ESI): 166 ([M-H]-,
29.9% In N,N-dimethyl-formamide; at 20℃; for 24h; To a solution of compound 3 (300.0 mg, 2.40 mmol) in DMF (12.0 mL) was added carbon disulfide (365 mg, 4.80 mmol). After the mixture was stirred at 20 C for 24 h, it was concentrated and washed with water (15 mL x 2), and solid was collected to give compound 2 (120 mg, 29.9% yield) as a gray solid which was used directly in next step.
  • 96
  • [ 4224-70-8 ]
  • [ 7390-62-7 ]
  • C11H15N5O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃;pH Ca.8; General procedure: These compounds were each prepared by a condensation under peptide coupling reaction condition of the amino group of compound 1a and a carboxyl intermediate which was derived from a nucleophilic substitution reaction between an ω-bromo-alkanoic acid and a thiol. The following is a typical synthetic procedure: to a stirred solution of a thiol (R-SH) (0.1 mmol) in a mixture of MeOH (degassed with nitrogen bubbling for 2h right before use) (3.3 mL) and an 1.0 M triethylammonium bicarbonate buffer (pH~8) (3.3 mL) was added at room temperature an ω-bromo-alkanoic acid (0.1 mmol), and the whole reaction mixture was stirred at room temperature overnight before being concentrated in vacuo to remove MeOH. The resulting aqueous solution was lyophilized to give a solid which was subsequently used for the next step of reaction without purification. To this solid was added HBTU (0.1 mmol), HOBt (0.1 mmol), and a 0.4 M solution of NMM in DMF (0.4 mL) to dissolve all the materials; the resulting solution was then added to compound 1a (0.02 mmol) (pre-neutralized with triethylamine while in a MeOH solution followed by MeOH removal in vacuo), and the whole reaction mixture was stirred at room temperature for 2h before cold diethyl ether was added to precipitate out the crude 1-16 which were then each purified by reversed-phase high performance liquid chromatography (RP-HPLC) on a semi-preparative C18 column (1 x 25 cm, 5 µm). The column was eluted with a gradient of ddH2O containing 0.05% (v/v) trifluoroacetic acid (TFA) and acetonitrile containing 0.05% (v/v) TFA at 4.5mL/min and was monitored at 214 nm. The pooled HPLC fractions were then concentrated in vacuo to remove acetonitrile and the remaining aqueous solution was lyophilized to give 1-16 each as a puffy white solid. The purified 1-16 were each >95% pure based on RP-HPLC analysis on an analytical C18 column (0.46 x 25 cm, 5 μm). The exact masses of the purified 1-16 were confirmed by high-resolution mass spectrometry (HRMS) analysis (see Table 1).
  • 97
  • [ 17696-11-6 ]
  • [ 7390-62-7 ]
  • C13H19N5O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃;pH Ca.8; General procedure: These compounds were each prepared by a condensation under peptide coupling reaction condition of the amino group of compound 1a and a carboxyl intermediate which was derived from a nucleophilic substitution reaction between an ω-bromo-alkanoic acid and a thiol. The following is a typical synthetic procedure: to a stirred solution of a thiol (R-SH) (0.1 mmol) in a mixture of MeOH (degassed with nitrogen bubbling for 2h right before use) (3.3 mL) and an 1.0 M triethylammonium bicarbonate buffer (pH~8) (3.3 mL) was added at room temperature an ω-bromo-alkanoic acid (0.1 mmol), and the whole reaction mixture was stirred at room temperature overnight before being concentrated in vacuo to remove MeOH. The resulting aqueous solution was lyophilized to give a solid which was subsequently used for the next step of reaction without purification. To this solid was added HBTU (0.1 mmol), HOBt (0.1 mmol), and a 0.4 M solution of NMM in DMF (0.4 mL) to dissolve all the materials; the resulting solution was then added to compound 1a (0.02 mmol) (pre-neutralized with triethylamine while in a MeOH solution followed by MeOH removal in vacuo), and the whole reaction mixture was stirred at room temperature for 2h before cold diethyl ether was added to precipitate out the crude 1-16 which were then each purified by reversed-phase high performance liquid chromatography (RP-HPLC) on a semi-preparative C18 column (1 x 25 cm, 5 µm). The column was eluted with a gradient of ddH2O containing 0.05% (v/v) trifluoroacetic acid (TFA) and acetonitrile containing 0.05% (v/v) TFA at 4.5mL/min and was monitored at 214 nm. The pooled HPLC fractions were then concentrated in vacuo to remove acetonitrile and the remaining aqueous solution was lyophilized to give 1-16 each as a puffy white solid. The purified 1-16 were each >95% pure based on RP-HPLC analysis on an analytical C18 column (0.46 x 25 cm, 5 μm). The exact masses of the purified 1-16 were confirmed by high-resolution mass spectrometry (HRMS) analysis (see Table 1).
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