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[ CAS No. 61135-33-9 ] {[proInfo.proName]}

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Chemical Structure| 61135-33-9
Chemical Structure| 61135-33-9
Structure of 61135-33-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 61135-33-9 ]

CAS No. :61135-33-9 MDL No. :MFCD01675687
Formula : C11H12N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :CDEURGJCGCHYFH-DJLDLDEBSA-N
M.W : 252.22 Pubchem ID :472172
Synonyms :
5-EdU;2'-Deoxy-5-ethynyluridine;EdU

Calculated chemistry of [ 61135-33-9 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 61.04
TPSA : 104.55 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) : -8.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : -1.29
Log Po/w (WLOGP) : -2.09
Log Po/w (MLOGP) : -1.34
Log Po/w (SILICOS-IT) : 0.13
Consensus Log Po/w : -0.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.71
Solubility : 49.7 mg/ml ; 0.197 mol/l
Class : Very soluble
Log S (Ali) : -0.41
Solubility : 98.6 mg/ml ; 0.391 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.14
Solubility : 181.0 mg/ml ; 0.719 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.79

Safety of [ 61135-33-9 ]

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

Application In Synthesis of [ 61135-33-9 ]

* 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 [ 61135-33-9 ]

[ 61135-33-9 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 2166-14-5 ]
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  • [ 100020-99-3 ]
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  • [ 100021-04-3 ]
  • [ 100021-03-2 ]
  • 4
  • [ 78731-54-1 ]
  • [ 78731-56-3 ]
  • [ 61135-33-9 ]
  • 5
  • [(2R,3S,5R)-3-Acetoxy-5-(5-ethynyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetic acid ethyl ester [ No CAS ]
  • [ 117627-05-1 ]
  • [ 61135-33-9 ]
  • 6
  • [ 151362-01-5 ]
  • [ 61135-33-9 ]
YieldReaction ConditionsOperation in experiment
395 mg With methanol; sodium methylate; at 25℃; for 2h;Inert atmosphere; 5-Ethynyl-2?-deoxyuridine (0289) 5-Iodo-2?-deoxyuridine (5, 1.0 g, 2.82 mmol) was dissolved in MeCN/Et3N (66 mL of 1:1, v/v) under argon atmosphere. Trimethylsilylacetylene (1.6 mL, 11.3 mmol), bis-(triphenylphosphine)-palladium(II) chloride (42.2 mg, 0.60 mmol), and CuI (28 mg, 0.15 mmol) were added, and the mixture was heated for 3.5 h in the flask immersed into a preheated oil bath (50 C.). The solvents were removed in vacuo to give a residue that was purified by silica gel flash column chromatography. Elution with CHCl3/MeOH (9:1, v/v) afforded trimethylsilyl intermediate as a solid (0.75 g, 82%). To the solution of this intermediate (0.7 g, 2.16 mmol) in anhydrous MeOH (16 mL) under argon atmosphere, a solution of NaOMe in MeOH (145 mL of 0.05 N) was added, and the reaction was stirred at 25 C. for 2 h. The pH of the solution was adjusted to 5-6 using Dowex 50 WX8-200 (H+), the mixture was filtered, and concentrated in vacuo to give a residue that was purified by silica gel column flash chromatography using CHCl3/MeOH (8:2, v/v) as eluent to yield 5-ethynyl-2?-deoxyuridine (EdU) as a white solid (395 mg, 73%); 1H NMR (DMSO-d6) delta 11.62 (s, 1H, NH), 8.29 (s, 1H, H-6), 6.10 (dd, J=6.56, 6.56 Hz, 1H, H-1?), 5.24 (d, J=4.31 Hz, 1H, C-3? OH), 5.12 (t, J=4.91 Hz, 1H, C-5? OH), 4.23 (m, 1H, H-3?), 4.10 (s, 1H, CCH), 3.79 (q, J=3.25, 3.25, 3.26 Hz, 1H, H-4?), 3.59 (m, 2H, H-5?, H-5?), 2.16 (m, 2H, H-2?, H-2?). HRMS calcd for C11H11N2O14 251.0673 (M-H)-. found 251.0683.
  • 7
  • [ 461-96-1 ]
  • [ 61135-33-9 ]
  • 5-(3,5-Difluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione [ No CAS ]
  • 8
  • [ 402-43-7 ]
  • [ 61135-33-9 ]
  • 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(4-trifluoromethyl-phenylethynyl)-1H-pyrimidine-2,4-dione [ No CAS ]
  • 9
  • [ 328-70-1 ]
  • [ 61135-33-9 ]
  • 5-<2-<3,5-Bis(trifluoromethyl)phenyl>ethynyl>-2'-deoxyuridine [ No CAS ]
  • 11
  • [ 61135-33-9 ]
  • 5-ethynyl-2'-deoxyuridine-5'-phosphorodichloridate [ No CAS ]
  • 12
  • [ 61135-33-9 ]
  • [ 79897-02-2 ]
  • 14
  • [ 61135-33-9 ]
  • [ 15176-29-1 ]
  • 15
  • [ 61135-33-9 ]
  • [ 55520-67-7 ]
  • 17
  • [ 61135-33-9 ]
  • [ 139546-03-5 ]
  • 18
  • [ 69075-43-0 ]
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  • 19
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  • [ 933448-51-2 ]
  • 20
  • [ 29558-78-9 ]
  • [ 61135-33-9 ]
  • [ 1034147-10-8 ]
  • 22
  • [ 61135-33-9 ]
  • 5-[4-(4'-(2-fluoroethoxy)phenyl)phenyl]ethynyl}-2'-deoxyuridine [ No CAS ]
  • 24
  • [ 61135-33-9 ]
  • [ 933448-55-6 ]
  • 25
  • [ 61135-33-9 ]
  • [10-(10-[5-ethyl-2',5'-dideoxyuridine-5'-methyl]-carbamoyl}-decylcarbamoyl)-decyl]-methoxycarbonylmethyl-amino}-acetic acid [ No CAS ]
  • 26
  • [ 61135-33-9 ]
  • [ 90760-95-5 ]
  • 27
  • [ 61135-33-9 ]
  • 3-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[((E)-3-propenyl)-phenyl]-3H-furo[2,3-d]pyrimidin-2-one [ No CAS ]
  • 28
  • [ 61135-33-9 ]
  • 6-[((E)-3-But-1-enyl)-phenyl]-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3H-furo[2,3-d]pyrimidin-2-one [ No CAS ]
  • 29
  • [ 61135-33-9 ]
  • 3-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[((E)-3-pent-1-enyl)-phenyl]-3H-furo[2,3-d]pyrimidin-2-one [ No CAS ]
  • 30
  • [ 149798-19-6 ]
  • [ 61135-33-9 ]
  • 31
  • [ 54-42-2 ]
  • CH3(CH2)3CCX [ No CAS ]
  • [ 61135-33-9 ]
  • 32
  • [ 61135-33-9 ]
  • [ 261966-78-3 ]
  • 33
  • [ 5168-36-5 ]
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  • 34
  • [ 151361-85-2 ]
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  • 35
  • [ 117626-99-0 ]
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  • 36
  • [ 117626-97-8 ]
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  • 37
  • [ 117626-98-9 ]
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  • 38
  • [ 61135-33-9 ]
  • [ 117627-00-6 ]
  • 39
  • [ 61135-33-9 ]
  • [(2R,3S,5R)-3-Acetoxy-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetic acid ethyl ester [ No CAS ]
  • 40
  • [ 61135-33-9 ]
  • [ 287980-23-8 ]
  • 41
  • [ 61135-33-9 ]
  • Acetic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
  • 42
  • [ 61135-33-9 ]
  • [ 117626-80-9 ]
  • 45
  • [ 61135-33-9 ]
  • [ 111289-87-3 ]
YieldReaction ConditionsOperation in experiment
28% 5-Ethynyl-2?-deoxyuridine-5?-triphosphate (0290) EdU was dried by coevaporation with dry pyridine, and left over P2O5 under vacuo overnight. The compound (75 mg, 0.3 mmol) was dissolved in solution of trimethylphosphate (2 mL), cooled in ice-bath, and a powdered Proton Sponge (96.4 mg, 0.45 mmol) was added followed by POCl3 (30 muL, 0.33 mmol). After 2 h of stirring, a solution of tributylammonium pyrophosphate in DMF (3 mL, 1.5 mmol) containing tributylamine (300 muL, 1.26 mmol) was quickly added to the reaction mixture. After 2 min of stirring mixture was poured into 30 mL of 0.2 M TEAB, stirred and evaporated to dryness. Proton-Sponge was removed on small column with Dowex 50 WX8-200 (Na+). The crude product was then purified by preparative HPLC with 70% MeCN/0.1M TEAB (2-10 linear gradient) to give a residue which was dissolved in water, and passed through a small column of Dowex 50 WX8-200 (Na+). Fractions containing product were combined and lyophilized to give the product as a white powder (46.5 mg, 28%). 1H NMR (D2O) delta 8.02 (s, 1H, H-6), 6.76 (t, J=6.59 Hz, 1H, H-1?), 4.44 (m, 1H, H-3?), 4.00 (m, 3H, H-4?, H-5?, H-5?), 3.39 (s, 1H, CCH), 2.12 (m, 2H, H-2?, H-2?). 31P NMR (243 MHz, D2O) delta ppm -8.94 (d, J=20.38 Hz), -10.49 (d, J=20.19 Hz), -22.16 (t, J=20.17 Hz). HRMS calcd for C11H14N2O14P3 490.9663 (M-H)-. found 490.9673.
General procedure: Proton sponge (1.5 equiv) and free nucleoside (1 equiv) were dissolved in trimethylphosphate (0.3 M) and cooled to -20 C. POCl3(1.5 equiv) was added dropwise, and then the purple slurry was stirred at -20 C for 2 h. Tributylamine (6.2 equiv) was added, followed by a solution of tributylammonium pyrophosphate (5.0 equiv) in DMF (0.5 M). After 5 min, the reaction was quenched by the addition of 0.5 M aqueous Et3NH2CO3(20 vol-equiv) and the resulting solution was lyophilized. Purification through reverse-phase (C18) HPLC (4-35% CH3CN in 0.1 M Et3NH2CO3, pH 7.5), followed by lyophilization, afforded the triphosphate as a solid
  • 46
  • tetraethylammonium fluoride hydrate [ No CAS ]
  • [ 151362-01-5 ]
  • [ 61135-33-9 ]
YieldReaction ConditionsOperation in experiment
71% In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; dichloromethane; (b) 2'-Deoxy-5-Ethynyluridine The title compound was prepared according to a modification of the procedure of Morris J. Robbins and Philip J Barr, J. Org. Chem., 1983, 48, 1854-1862. A mixture of 2'-deoxy-5-(2-(trimethylsilyl)ethynyl)uridine (2.4 mmol) and tetraethyl ammonium fluoride hydrate (Aldrich Chemical Co., Milwaukee, Wis.) (2.4 mmol) was magnetically stirred in 10 ml dry acetonitrile (Aldrich) for 1 hour. The solution was applied directly to a column (2.5*30 cm) of 100 g silica gel (230-400 mesh) packed in dichloromethane. The column was eluted with 3% methanol in dichloromethane to obtain pure product (1.7 mmol, 71% yield) as an off-white solid after evaporation of solvent. 1R (KBr) 2120 cm-1, C?C stretch. 1 H NMR (300 MHz, DMSO-d6) delta 11.58-11.65 (bs, 1H, NH), 8.30 (s, 1H,H6), 6.13-6.08 (t, 1H, H1', J=6.55 Hz), 5.26-5.24 (d, 1H, 3'-OH, J=4.3 Hz), 5.15-5.12 (t, 1H, 5'-OH, J=4.90 Hz), 4.26-4.21 (m - 5 lines, 1H, H3'), 4.11 (s, 1h, acetylenic H), 3.82-3.79 (q, 1H, H4'), 3.63-3.56 (m, 2H, H5" and H5'), 2.15-2.12 (m, 2H, H2" and H2').
  • 47
  • [ 124-63-0 ]
  • [ 61135-33-9 ]
  • [ 107667-05-0 ]
YieldReaction ConditionsOperation in experiment
93% In pyridine; ethanol; EXAMPLE 4 2'-Deoxy-3'-5'-di-O-methanesulphonyl-5-ethynyluridine To a stirred solution of <strong>[61135-33-9]2'-deoxy-5-ethynyluridine</strong> in dry pyridine at 0 C. was added methanesulphonylchloride (3.5 equivalents) and the whole was stirred at room temperature for 3 hrs. The solution was added to iced water and the solid filtered off. This was washed with water and digested in hot ethanol to give the title compound in 93% yield. M.p. 184-186 C. NMR: deltad6 DMSO 11.75 (1H, d, NH), 8.05 (1H, s, H-6), 6.15 (1H, bt, H-1') 5.3 (1H, m, H-3'), 4.6-4.3 (3H, m, H-4', 8H-5'), 3.35 (6H, s, CH3 SO2), 3.25 (1H, s, acetylenic H), 2.7-2.4 ppm (2H, m, H-2').
  • 48
  • dichloromethane hydrate [ No CAS ]
  • [ 3282-30-2 ]
  • [ 61135-33-9 ]
  • [ 107684-79-7 ]
YieldReaction ConditionsOperation in experiment
In pyridine; methanol; dichloromethane; EXAMPLE 2 2'-Deoxy-5-ethynyl-5'-O-pivaloyluridine and 2'-Deoxy-5-ethynyl-3',5'-di-O-pivaloyl uridine Pivaloyl chloride (0.3 ml, 2.56 mmoles) was added to a cooled, stirred solution of <strong>[61135-33-9]2'-deoxy-5-ethynyluridine</strong> (0.5 g, 1.98 mmols) in dry pyridine (5 ml) and stirring was maintained at room temperature for 3 hours. TLC in CH2 Cl2 /MeOH (19:1) revealed complete reaction. The mixture was poured onto ice/water, methylene chloride added, the organic layer separated and washed with water, dried with sodium sulphate and evaporated to dryness. The residue was chromatographed on silica gel eluted with CH2 Cl2 /MeOH. The first product was triturated with hexane to give 2'-deoxy-3',5'-di-O-pivaloyl-5-ethynyluridine. M.p. 151 C. NMR: deltaCDCl3 7.8(1H, s, H-6), 6.6-6.0(3H, m, H-1', NH, OH-3'), 4.7-4.1 (4H, m, H-3', H-4' and H-5'), 3.22 (1H, s, acetylenic H), 2.6 (1H, m H-2'), 2.3 (1H, m, H-2'), 1.3 ppm (9H, s, tBu-H)
  • 49
  • [ 61135-33-9 ]
  • [ 100021-00-9 ]
YieldReaction ConditionsOperation in experiment
91% In ethanol; acetic anhydride; EXAMPLE 3 2'-Deoxy-3'-5'-di-O-acetyl-5-ethynyluridine To a stirred solution of <strong>[61135-33-9]2'-deoxy-5-ethynyluridine</strong> (0.5 g, 2 mmoles) in dry pryidine (8 ml) at 0 C. was added acetic anhydride (0.6 g, 6 mmols) and stirring maintained at room temperature overnight. The solvent was evaporated in vacuo and coevaporated with ethanol. The residual mass was triturated with ethanol, filtered and recrystallized from ethanol to give the title compound (0.61 g, 91%). Mp 138-140 C. NMR: deltaCDCl3 8.4 (1H, s, NH), 7.9 (1H, s, H-6), 6.3 (1H, t, H-1'), 5.8 (1H, m, H-3'), 4.35 (3H, m, H-4' and H-5'), 3.2 (1H, s, acetylenic H), 2.35 (2H, m, H-2'), 2.12 ppm (6H, d, OCH3).
91% With acetic anhydride; In pyridine; ethanol; Example 3 : 2'-Deoxy-3'-5'-di-O-acetyl-5-ethynyluridine To a stirred solution of <strong>[61135-33-9]2'-deoxy-5-ethynyluridine</strong> (0.5g, 2mmoles) in dry pyridine (8ml) at 0C was added acetic anhydride (0.6g, 6mmols) and stirring maintained at room temperature overnight. The solvent was evaporated in vacuo and coevaporated with ethanol. The residual mass was triturated with ethanol, filtered and recrystallized from ethanol to give the title compound (0.61g, 91%). Mp 138-140C NMR; delta CDCl3 8.4 (1H, s, NH), 7.9 (1H, s, H-6), 6.3 (1H,t,H-1'), 5.8 (1H,m,H-3'), 4.35 (3H,m,H-4' and H-5'), 3.2 (1H,s, acetylenic H), 2.35 (2H,m, H-2'), 2.12 ppm (6H,d, OCH3).
  • 50
  • dichloromethane hydrate [ No CAS ]
  • [ 3282-30-2 ]
  • [ 61135-33-9 ]
  • [ 107667-04-9 ]
  • [ 107684-79-7 ]
YieldReaction ConditionsOperation in experiment
In pyridine; CH2Cl2/MeOH; Example 2 : 2'-Deoxy-5-ethynyl-5'-O-pivaloyluridine and 2'-Deoxy-5-ethynyl-3',5'-di-O-pivaloyl uridine Pivaloyl chloride (0.31ml, 2.56mmoles) was added to a cooled, stirred solution of <strong>[61135-33-9]2'-deoxy-5-ethynyluridine</strong> (0.5g, 1.98mmols) in dry pyridine (5ml) and stirring was maintained at room temperature for 3 hours. TLC in CH2Cl2/MeOH (19:1) revealed complete reaction. The mixture was poured onto ice/water, methylene chloride added, the organic layer separated and washed with water, dried with sodium sulphate and evaporated to dryness. The residue was chromatographed on silica gel eluted with CH2Cl2/MeOH. The first product eluted was triturated with hexane to give 2'-Deoxy-3',5'-di- O -pivaloyl-5-ethynyluridine. M.p. 151C. NMR: delta CDCl3 7.8 (1H,s,H-6), 6.6-6.0(3H, m, H-1',NH,OH-3'), 4.7-4.1 (4H, m, H-3',H-4' and H-5'), 3.22 (1H,s, acetylenic H), 2.6 (1H,m,H-2'), 2.3 (1H,m,H-2'), 1.3ppm (9H, s, tBu-H) The second product eluted was triturated with hexane to give 2'-deoxy-5-ethynyl-5'-O-pivaloyl-uridine. M.p. 64-66C. NMR: deltaCDCl3 8.65 (1H,bs,NH), 7.8 (1H,s,H-6), 6.2 (1H,dd,H-1'), 5.2 (1H,m,H-3'), 4.5-4.2 (3H,m,H-4' and H-5'), 3.18 (1H,s, acetylenic H), 2.6(1H,m, H-2'), 2.1 (1H,m, H-2'), 1.2 ppm (18H,d,tBu-H).
  • 51
  • [ 540-38-5 ]
  • [ 61135-33-9 ]
  • [ 1002760-28-2 ]
  • C23H20N2O7 [ No CAS ]
  • 52
  • [ 54-42-2 ]
  • [ 74-86-2 ]
  • [ 61135-33-9 ]
  • 53
  • [ 17084-13-8 ]
  • [ 178314-92-6 ]
  • [ 61135-33-9 ]
  • Ru(C5H4NC5H4N)2(C12H7N2C2C4HO2N2HC4H5OOHCH2OH)(2+)*2PF6(1-)=Ru(C10H8N2)2(C12H7N2C2C4O2HN2HC4H5O2HCH2OH)(PF6)2 [ No CAS ]
  • 54
  • [ 17084-13-8 ]
  • [ 178314-92-6 ]
  • [ 61135-33-9 ]
  • Ru(C5H4NC5H4N)2(C12H7N2C2C4HO2N2HC4H5OOHCH2OH)(2+)*2PF6(1-)=Ru(C10H8N2)2(C12H7N2C2C4O2HN2HC4H5O2HCH2OH)(PF6)2 [ No CAS ]
  • 55
  • [ 17084-13-8 ]
  • [ 178314-92-6 ]
  • [ 61135-33-9 ]
  • Ru(C5H4NC5H4N)2(C12H7N2C2C4HO2N2HC4H5OOHCH2OH)(2+)*2PF6(1-)=Ru(C10H8N2)2(C12H7N2C2C4O2HN2HC4H5O2HCH2OH)(PF6)2 [ No CAS ]
  • 56
  • [ 17084-13-8 ]
  • [ 201653-00-1 ]
  • [ 61135-33-9 ]
  • Os(C5H4NC5H4N)2(C12H7N2C2C4HO2N2HC4H5OOHCH2OH)(2+)*2PF6(1-)=Os(C10H8N2)2(C12H7N2C2C4O2HN2HC4H5O2HCH2OH)(PF6)2 [ No CAS ]
  • 57
  • [ 15226-74-1 ]
  • [ 61135-33-9 ]
  • hexacarbonyl dicobalt 5-ethynyl-2'-deoxyuridine [ No CAS ]
  • 58
  • 1-iodo-4-(prop-1-en-1-yl)benzene [ No CAS ]
  • [ 61135-33-9 ]
  • [ 1159683-93-8 ]
  • 59
  • [ 1159683-86-9 ]
  • [ 61135-33-9 ]
  • [ 1159683-94-9 ]
  • 60
  • [ 1159683-88-1 ]
  • [ 61135-33-9 ]
  • [ 1159683-96-1 ]
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  • [ 1159683-89-2 ]
  • [ 61135-33-9 ]
  • [ 1159683-97-2 ]
  • 62
  • [ 199450-86-7 ]
  • [ 61135-33-9 ]
  • [ 1159683-99-4 ]
  • 63
  • (E)-1-iodo-2-(prop-1-enyl)benzene [ No CAS ]
  • [ 61135-33-9 ]
  • [ 1159683-91-6 ]
  • 64
  • [ 54-42-2 ]
  • [ 61135-33-9 ]
  • [ 1187880-23-4 ]
  • 66
  • [ 1237723-01-1 ]
  • [ 61135-33-9 ]
  • [ 1237723-03-3 ]
  • 67
  • 5'-d(AGTAT[5-ethynyl-U]GACCTA)-3' [ No CAS ]
  • [ 959326-89-7 ]
  • [ 961-07-9 ]
  • [ 61135-33-9 ]
  • [ 50-89-5 ]
  • [ 958-09-8 ]
  • 68
  • [ 63697-61-0 ]
  • [ 61135-33-9 ]
  • 1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[1-(2,2,6,6-tetramethyl-1-yloxypiperidin-4-yl)-1,2,3-triazol-4-yl]uracil [ No CAS ]
  • 69
  • [ 894792-94-0 ]
  • [ 61135-33-9 ]
  • [ 913183-79-6 ]
  • 70
  • [ 894793-02-3 ]
  • [ 61135-33-9 ]
  • [ 913183-81-0 ]
  • 71
  • 4-(2-(9-bromoanthracen-10-yl)ethynyl)-N,N-dimethylbenzenamine [ No CAS ]
  • [ 61135-33-9 ]
  • [ 1374418-30-0 ]
  • 72
  • [ 1374418-18-4 ]
  • [ 61135-33-9 ]
  • [ 1374418-24-2 ]
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  • [ 1374418-19-5 ]
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  • [ 1374418-25-3 ]
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  • [ 1374418-20-8 ]
  • [ 61135-33-9 ]
  • [ 1374418-26-4 ]
  • 75
  • [ 1374418-21-9 ]
  • [ 61135-33-9 ]
  • [ 1374418-27-5 ]
  • 76
  • [ 1374418-22-0 ]
  • [ 61135-33-9 ]
  • [ 1374418-28-6 ]
  • 77
  • [ 1374418-23-1 ]
  • [ 61135-33-9 ]
  • [ 1374418-29-7 ]
  • 79
  • [ 85267-60-3 ]
  • [ 61135-33-9 ]
  • 80
  • [ 100021-00-9 ]
  • [ 61135-33-9 ]
  • 81
  • [ 1956-30-5 ]
  • [ 61135-33-9 ]
  • 82
  • [ 13030-62-1 ]
  • [ 61135-33-9 ]
  • 83
  • [ 16650-14-9 ]
  • [ 61135-33-9 ]
  • C30H29N3O6 [ No CAS ]
  • 84
  • [ 59989-18-3 ]
  • [ 50-89-5 ]
  • [ 61135-33-9 ]
  • 85
  • [ 61135-33-9 ]
  • [ 1610541-85-9 ]
  • 86
  • [ 61135-33-9 ]
  • [ 1610541-97-3 ]
  • 87
  • [ 61135-33-9 ]
  • [ 1610542-01-2 ]
  • 88
  • [ 624-38-4 ]
  • [ 61135-33-9 ]
  • [ 1610541-84-8 ]
YieldReaction ConditionsOperation in experiment
58% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; 5-Ethynyl-dU (0.17 g, 0.674 mmol) was dissolved in DMF (5 mL) and maintained under nitrogen atmosphere. To this solution NEt3 (0.427 mL, 3.03 mmol), 1,4-diiodobenzene (1.12 g, 3.37 mmol), Pd(Ph3P)4 (78 mg, 0.068 mmol) and Cul (25.7 mg, 0.135 mmol) were added sequentially with stirring under nitrogen. The reaction was continued at rt for 2 h and TLC (10% MeOH in DCM) and LCMS (ES+) indicated complete disappearance of starting material. After removing the solvent under reduced pressure, the residue was chromatographed on silica gel column using 0 - 20% MeOH gradient over DCM) to get pure product (0.178 g, 58%). TLC: (10% MeOH in DCM): Rf = 0.68. LCMS (ES+): (M+H) calculated mass: 455.22 and observed mass: 454.67. 1H-NMR (DMSO-d6): delta 11.70 (bs, 1H, 3-NH-), 8.37 (s, 1H, 6-H), 7.75 (d, 2H, Ar-H), 7.23 (d, 2H, Ar-H), 6.09 (t, 1H, l'-H), 5.44 (d, 1H, 2'-OH), 5.28 (t, 1H, 5'-OH), 4.24 (m, 1H, 4H), 3.53 - 3.80 (m, 3H, 3'-H, 5'-H & 5"-H), 2.45 (m, 1H, 2'-H), 2.14 (m, 1H, 2' & 2"-H)
Same Skeleton Products
Historical Records