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CAS No. : | 34671-83-5 | MDL No. : | MFCD00014600 |
Formula : | C8H6N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HKOAFLAGUQUJQG-UHFFFAOYSA-N |
M.W : | 158.16 | Pubchem ID : | 123444 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.06 |
TPSA : | 51.56 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.14 cm/s |
Log Po/w (iLOGP) : | 1.46 |
Log Po/w (XLOGP3) : | 0.18 |
Log Po/w (WLOGP) : | 0.93 |
Log Po/w (MLOGP) : | -0.36 |
Log Po/w (SILICOS-IT) : | 1.51 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.61 |
Solubility : | 3.9 mg/ml ; 0.0247 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.82 |
Solubility : | 23.9 mg/ml ; 0.151 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.41 |
Solubility : | 0.0614 mg/ml ; 0.000388 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.42 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With zinc;5-trimethylsilyl-2,2'-bipyridine; nickel dibromide; In 1-methyl-pyrrolidin-2-one; at 20 - 70℃;Inert atmosphere; | <Example 21> To a glass reaction container equipped with a cooling apparatus, 15.3 mg of nickel bromide, 19.2 mg of 5-trimethylsilyl-2,2'-bipyridine and 91.6 mg of zinc powder were added in an atmosphere of nitrogen at room temperature. To the obtained mixture, 80.2 mg of 2-chloropyrimidine and 5 mL of N-methyl-2-pyrrolidone were added. The obtained mixture was reacted at 70C for 2 hours to obtain a reaction mixture containing 2,2'-bipyrimidine. The yield of 2,2'-bipyrimidine was 7.9 mg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | [Ru(Mebimpy)Cl3] (700 mg, 1.28 mmol) and bpm (203 mg, 1.28 mmol) were suspended in 60 mL of 2:1 EtOH:H2O and the mixture was degassed by argon bubbling. Triethylamine (2.5 mL) was added with a syringe and the suspension was heated at reflux for 4 hours. 20 mL of 20% aqueous LiCl were added and the brown microcrystalline solid formed was isolated by filtration and washed with water and ether. Yield: 728 mg, 85%. 1H-NMR (CD3CN): delta 10.89-10.91 (dd, 1H), 9.42-9.44 (dd, 1H), 8.58 (d, 3H), 8.13-8.18 (m, 2H), 7.70-7.72 (dd, 1H), 7.63 (d, 2H), 7.39-7.44 (td, 2H), 7.09-7.13 (t, 2H), 6.99-7.02 (t, 1H), 6.24 (d, 2H), 4.40 (s, 6H, 2CH3). This compound was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: Er(fod)3 (0.067 g, ?0.0636 mmol) was dissolved in 10 mL absolute ethanol. To this solution was slowly added a solution of 2,2?-bipyrimidine (0.010 g, ?0.063 mmol) in 10 mL absolute ethanol. The reaction mixture was kept on a magnetic stirrer at ambient temperature and continuously stirred for approximately 1 h. To this reaction mixture was then slowly added a solution of Tm(fod)3 (0.067 g, ?0.063 mmol) dissolved in 10 mL absolute ethanol. The reaction mixture was again placed on the magnetic stirrer and continuously stirred for 3 h at ambient temperature. The resulting solution (approx. 20 mL) was covered and left for slow evaporation at room temperature. The discrete and homogeneous pink coloured crystals appeared after 24 h. The crystals were filtered off and dried in vacuo over P4O10. The product was recrystallized from absolute ethanol: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: Er(fod)3 (0.067 g, ?0.0636 mmol) was dissolved in 10 mL absolute ethanol. To this solution was slowly added a solution of 2,2?-bipyrimidine (0.010 g, ?0.063 mmol) in 10 mL absolute ethanol. The reaction mixture was kept on a magnetic stirrer at ambient temperature and continuously stirred for approximately 1 h. To this reaction mixture was then slowly added a solution of Tm(fod)3 (0.067 g, ?0.063 mmol) dissolved in 10 mL absolute ethanol. The reaction mixture was again placed on the magnetic stirrer and continuously stirred for 3 h at ambient temperature. The resulting solution (approx. 20 mL) was covered and left for slow evaporation at room temperature. The discrete and homogeneous pink coloured crystals appeared after 24 h. The crystals were filtered off and dried in vacuo over P4O10. The product was recrystallized from absolute ethanol: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: Er(fod)3 (0.067 g, ?0.0636 mmol) was dissolved in 10 mL absolute ethanol. To this solution was slowly added a solution of 2,2?-bipyrimidine (0.010 g, ?0.063 mmol) in 10 mL absolute ethanol. The reaction mixture was kept on a magnetic stirrer at ambient temperature and continuously stirred for approximately 1 h. To this reaction mixture was then slowly added a solution of Tm(fod)3 (0.067 g, ?0.063 mmol) dissolved in 10 mL absolute ethanol. The reaction mixture was again placed on the magnetic stirrer and continuously stirred for 3 h at ambient temperature. The resulting solution (approx. 20 mL) was covered and left for slow evaporation at room temperature. The discrete and homogeneous pink coloured crystals appeared after 24 h. The crystals were filtered off and dried in vacuo over P4O10. The product was recrystallized from absolute ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane;Inert atmosphere; | General procedure: Under nitrogen (glovebox), a counter solventwas allowed to slowly diffuse into a solution containing the ligand(1 equiv.) and the cis-[Ti(dpbpol)2(HOiPr)2] complex (5 mg) in aminimum amount of dry CH2Cl2 in a small vial. Crystals were obtained from CH2Cl2/diethyl ether or pentane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: Er(fod)3 (0.067 g, ?0.0636 mmol) was dissolved in 10 mL absolute ethanol. To this solution was slowly added a solution of 2,2?-bipyrimidine (0.010 g, ?0.063 mmol) in 10 mL absolute ethanol. The reaction mixture was kept on a magnetic stirrer at ambient temperature and continuously stirred for approximately 1 h. To this reaction mixture was then slowly added a solution of Tm(fod)3 (0.067 g, ?0.063 mmol) dissolved in 10 mL absolute ethanol. The reaction mixture was again placed on the magnetic stirrer and continuously stirred for 3 h at ambient temperature. The resulting solution (approx. 20 mL) was covered and left for slow evaporation at room temperature. The discrete and homogeneous pink coloured crystals appeared after 24 h. The crystals were filtered off and dried in vacuo over P4O10. The product was recrystallized from absolute ethanol: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: Er(fod)3 (0.067 g, ?0.0636 mmol) was dissolved in 10 mL absolute ethanol. To this solution was slowly added a solution of 2,2?-bipyrimidine (0.010 g, ?0.063 mmol) in 10 mL absolute ethanol. The reaction mixture was kept on a magnetic stirrer at ambient temperature and continuously stirred for approximately 1 h. To this reaction mixture was then slowly added a solution of Tm(fod)3 (0.067 g, ?0.063 mmol) dissolved in 10 mL absolute ethanol. The reaction mixture was again placed on the magnetic stirrer and continuously stirred for 3 h at ambient temperature. The resulting solution (approx. 20 mL) was covered and left for slow evaporation at room temperature. The discrete and homogeneous pink coloured crystals appeared after 24 h. The crystals were filtered off and dried in vacuo over P4O10. The product was recrystallized from absolute ethanol: Colour (Pink). Yield (?0.120 g, 83%); Elemental Anal. Calc. for ErTmC68H66F42O12N4: C, 36.05; H, 2.95; N, 2.47. Found: C, 36.26; H, 3.02; N, 2.49%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: Er(fod)3 (0.067 g, ?0.0636 mmol) was dissolved in 10 mL absolute ethanol. To this solution was slowly added a solution of 2,2?-bipyrimidine (0.010 g, ?0.063 mmol) in 10 mL absolute ethanol. The reaction mixture was kept on a magnetic stirrer at ambient temperature and continuously stirred for approximately 1 h. To this reaction mixture was then slowly added a solution of Tm(fod)3 (0.067 g, ?0.063 mmol) dissolved in 10 mL absolute ethanol. The reaction mixture was again placed on the magnetic stirrer and continuously stirred for 3 h at ambient temperature. The resulting solution (approx. 20 mL) was covered and left for slow evaporation at room temperature. The discrete and homogeneous pink coloured crystals appeared after 24 h. The crystals were filtered off and dried in vacuo over P4O10. The product was recrystallized from absolute ethanol: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: Er(fod)3 (0.067 g, ?0.0636 mmol) was dissolved in 10 mL absolute ethanol. To this solution was slowly added a solution of 2,2?-bipyrimidine (0.010 g, ?0.063 mmol) in 10 mL absolute ethanol. The reaction mixture was kept on a magnetic stirrer at ambient temperature and continuously stirred for approximately 1 h. To this reaction mixture was then slowly added a solution of Tm(fod)3 (0.067 g, ?0.063 mmol) dissolved in 10 mL absolute ethanol. The reaction mixture was again placed on the magnetic stirrer and continuously stirred for 3 h at ambient temperature. The resulting solution (approx. 20 mL) was covered and left for slow evaporation at room temperature. The discrete and homogeneous pink coloured crystals appeared after 24 h. The crystals were filtered off and dried in vacuo over P4O10. The product was recrystallized from absolute ethanol: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: Er(fod)3 (0.067 g, ?0.0636 mmol) was dissolved in 10 mL absolute ethanol. To this solution was slowly added a solution of 2,2?-bipyrimidine (0.010 g, ?0.063 mmol) in 10 mL absolute ethanol. The reaction mixture was kept on a magnetic stirrer at ambient temperature and continuously stirred for approximately 1 h. To this reaction mixture was then slowly added a solution of Tm(fod)3 (0.067 g, ?0.063 mmol) dissolved in 10 mL absolute ethanol. The reaction mixture was again placed on the magnetic stirrer and continuously stirred for 3 h at ambient temperature. The resulting solution (approx. 20 mL) was covered and left for slow evaporation at room temperature. The discrete and homogeneous pink coloured crystals appeared after 24 h. The crystals were filtered off and dried in vacuo over P4O10. The product was recrystallized from absolute ethanol: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With sodium hydroxide; In ethanol; water; at 60℃; for 1.5h; | General procedure: In a typical synthesis, 3equiv of 2-thenoyltrifluoroacetone were dissolved in absolute ethanol, 3equiv of an aqueous solution of NaOH were added and the mixture was stirred at 60C for 30min. One equivalent of bpm was then added, followed by an aqueous solution of the hydrated lanthanide nitrates (Ln=Tb) or chlorides (Ln=Gd, Dy, Er, Ho). The complexes precipitated within a few minutes, and the reaction mixture was further stirred for 1h at 60C. After filtration, the precipitates were washed with water and dried under vacuum. Recrystallization from methanol or a mixture of acetonitrile/methanol (1:5, v/v) afforded the final complexes after drying. (0006) [{Gd(tta)3}2(mu-bpm)] (1). Yield: 31%. Anal. Calc. for C56H30F18N4O12S6Gd2: C, 37.37; H, 1.68; N, 3.11. Found: C, 37.40; H, 1.75; N, 3.29%. (0007) [{Tb(tta)3}2(mu-bpm)] (2). Yield: 29%. Anal. Calc. for C56H30F18N4O12S6Tb2: C, 37.30; H, 1.68; N, 3.11. Found: C, 37.03; H, 1.75; N, 3.33%. (0008) [{Dy(tta)3}2(mu-bpm)] (3). Yield: 36%. Anal. Calc. for C56H30F18N4O12S6Dy2. C, 37.16; H, 1.67; N, 3.10. Found: C, 36.97; H, 1.64; N, 3.33%. (0009) [{Ho(tta)3}2(mu-bpm)] (4). Yield: 28%. Anal. Calc. for C56H30F18N4O12S6Ho2: C, 37.06; H, 1.67; N, 3.09. Found: C, 37.21; H, 1.76; N, 3.24%. (0010) [{Er(tta)3}2(mu-bpm)] (5). Yield: 34%. Anal. Calc. for C56H30F18N4O12S6Er2: C, 36.96; H, 1.66; N, 3.08. Found: C, 37.28; H, 1.72; N, 3.23%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With sodium hydroxide; In ethanol; water; at 60℃; for 1.5h; | General procedure: In a typical synthesis, 3equiv of 2-thenoyltrifluoroacetone were dissolved in absolute ethanol, 3equiv of an aqueous solution of NaOH were added and the mixture was stirred at 60C for 30min. One equivalent of bpm was then added, followed by an aqueous solution of the hydrated lanthanide nitrates (Ln=Tb) or chlorides (Ln=Gd, Dy, Er, Ho). The complexes precipitated within a few minutes, and the reaction mixture was further stirred for 1h at 60C. After filtration, the precipitates were washed with water and dried under vacuum. Recrystallization from methanol or a mixture of acetonitrile/methanol (1:5, v/v) afforded the final complexes after drying. (0006) [{Gd(tta)3}2(mu-bpm)] (1). Yield: 31%. Anal. Calc. for C56H30F18N4O12S6Gd2: C, 37.37; H, 1.68; N, 3.11. Found: C, 37.40; H, 1.75; N, 3.29%. (0007) [{Tb(tta)3}2(mu-bpm)] (2). Yield: 29%. Anal. Calc. for C56H30F18N4O12S6Tb2: C, 37.30; H, 1.68; N, 3.11. Found: C, 37.03; H, 1.75; N, 3.33%. (0008) [{Dy(tta)3}2(mu-bpm)] (3). Yield: 36%. Anal. Calc. for C56H30F18N4O12S6Dy2. C, 37.16; H, 1.67; N, 3.10. Found: C, 36.97; H, 1.64; N, 3.33%. (0009) [{Ho(tta)3}2(mu-bpm)] (4). Yield: 28%. Anal. Calc. for C56H30F18N4O12S6Ho2: C, 37.06; H, 1.67; N, 3.09. Found: C, 37.21; H, 1.76; N, 3.24%. (0010) [{Er(tta)3}2(mu-bpm)] (5). Yield: 34%. Anal. Calc. for C56H30F18N4O12S6Er2: C, 36.96; H, 1.66; N, 3.08. Found: C, 37.28; H, 1.72; N, 3.23%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With sodium hydroxide; In ethanol; water; at 60℃; for 1.5h; | General procedure: In a typical synthesis, 3equiv of 2-thenoyltrifluoroacetone were dissolved in absolute ethanol, 3equiv of an aqueous solution of NaOH were added and the mixture was stirred at 60C for 30min. One equivalent of bpm was then added, followed by an aqueous solution of the hydrated lanthanide nitrates (Ln=Tb) or chlorides (Ln=Gd, Dy, Er, Ho). The complexes precipitated within a few minutes, and the reaction mixture was further stirred for 1h at 60C. After filtration, the precipitates were washed with water and dried under vacuum. Recrystallization from methanol or a mixture of acetonitrile/methanol (1:5, v/v) afforded the final complexes after drying. (0006) [{Gd(tta)3}2(mu-bpm)] (1). Yield: 31%. Anal. Calc. for C56H30F18N4O12S6Gd2: C, 37.37; H, 1.68; N, 3.11. Found: C, 37.40; H, 1.75; N, 3.29%. (0007) [{Tb(tta)3}2(mu-bpm)] (2). Yield: 29%. Anal. Calc. for C56H30F18N4O12S6Tb2: C, 37.30; H, 1.68; N, 3.11. Found: C, 37.03; H, 1.75; N, 3.33%. (0008) [{Dy(tta)3}2(mu-bpm)] (3). Yield: 36%. Anal. Calc. for C56H30F18N4O12S6Dy2. C, 37.16; H, 1.67; N, 3.10. Found: C, 36.97; H, 1.64; N, 3.33%. (0009) [{Ho(tta)3}2(mu-bpm)] (4). Yield: 28%. Anal. Calc. for C56H30F18N4O12S6Ho2: C, 37.06; H, 1.67; N, 3.09. Found: C, 37.21; H, 1.76; N, 3.24%. (0010) [{Er(tta)3}2(mu-bpm)] (5). Yield: 34%. Anal. Calc. for C56H30F18N4O12S6Er2: C, 36.96; H, 1.66; N, 3.08. Found: C, 37.28; H, 1.72; N, 3.23%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With sodium hydroxide; In ethanol; water; at 60℃; for 1.5h; | General procedure: In a typical synthesis, 3equiv of 2-thenoyltrifluoroacetone were dissolved in absolute ethanol, 3equiv of an aqueous solution of NaOH were added and the mixture was stirred at 60C for 30min. One equivalent of bpm was then added, followed by an aqueous solution of the hydrated lanthanide nitrates (Ln=Tb) or chlorides (Ln=Gd, Dy, Er, Ho). The complexes precipitated within a few minutes, and the reaction mixture was further stirred for 1h at 60C. After filtration, the precipitates were washed with water and dried under vacuum. Recrystallization from methanol or a mixture of acetonitrile/methanol (1:5, v/v) afforded the final complexes after drying. (0006) [{Gd(tta)3}2(mu-bpm)] (1). Yield: 31%. Anal. Calc. for C56H30F18N4O12S6Gd2: C, 37.37; H, 1.68; N, 3.11. Found: C, 37.40; H, 1.75; N, 3.29%. (0007) [{Tb(tta)3}2(mu-bpm)] (2). Yield: 29%. Anal. Calc. for C56H30F18N4O12S6Tb2: C, 37.30; H, 1.68; N, 3.11. Found: C, 37.03; H, 1.75; N, 3.33%. (0008) [{Dy(tta)3}2(mu-bpm)] (3). Yield: 36%. Anal. Calc. for C56H30F18N4O12S6Dy2. C, 37.16; H, 1.67; N, 3.10. Found: C, 36.97; H, 1.64; N, 3.33%. (0009) [{Ho(tta)3}2(mu-bpm)] (4). Yield: 28%. Anal. Calc. for C56H30F18N4O12S6Ho2: C, 37.06; H, 1.67; N, 3.09. Found: C, 37.21; H, 1.76; N, 3.24%. (0010) [{Er(tta)3}2(mu-bpm)] (5). Yield: 34%. Anal. Calc. for C56H30F18N4O12S6Er2: C, 36.96; H, 1.66; N, 3.08. Found: C, 37.28; H, 1.72; N, 3.23%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With sodium hydroxide; In ethanol; water; at 60℃; for 1.5h; | General procedure: In a typical synthesis, 3equiv of 2-thenoyltrifluoroacetone were dissolved in absolute ethanol, 3equiv of an aqueous solution of NaOH were added and the mixture was stirred at 60C for 30min. One equivalent of bpm was then added, followed by an aqueous solution of the hydrated lanthanide nitrates (Ln=Tb) or chlorides (Ln=Gd, Dy, Er, Ho). The complexes precipitated within a few minutes, and the reaction mixture was further stirred for 1h at 60C. After filtration, the precipitates were washed with water and dried under vacuum. Recrystallization from methanol or a mixture of acetonitrile/methanol (1:5, v/v) afforded the final complexes after drying. (0006) [{Gd(tta)3}2(mu-bpm)] (1). Yield: 31%. Anal. Calc. for C56H30F18N4O12S6Gd2: C, 37.37; H, 1.68; N, 3.11. Found: C, 37.40; H, 1.75; N, 3.29%. (0007) [{Tb(tta)3}2(mu-bpm)] (2). Yield: 29%. Anal. Calc. for C56H30F18N4O12S6Tb2: C, 37.30; H, 1.68; N, 3.11. Found: C, 37.03; H, 1.75; N, 3.33%. (0008) [{Dy(tta)3}2(mu-bpm)] (3). Yield: 36%. Anal. Calc. for C56H30F18N4O12S6Dy2. C, 37.16; H, 1.67; N, 3.10. Found: C, 36.97; H, 1.64; N, 3.33%. (0009) [{Ho(tta)3}2(mu-bpm)] (4). Yield: 28%. Anal. Calc. for C56H30F18N4O12S6Ho2: C, 37.06; H, 1.67; N, 3.09. Found: C, 37.21; H, 1.76; N, 3.24%. (0010) [{Er(tta)3}2(mu-bpm)] (5). Yield: 34%. Anal. Calc. for C56H30F18N4O12S6Er2: C, 36.96; H, 1.66; N, 3.08. Found: C, 37.28; H, 1.72; N, 3.23%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | at 170℃; for 24h; | Hydrothermal reaction of cadmium chloride (0.402g, 2mmol) with 2-pyrimidinecarbonitrile (0.105g , 1mmol) and 2,2?-bipyrimidine as secondary ligand (0.158g, 1mmol) in water (14ml) at 170C for 24h followed by cooling down to room temperature over 2h, yield prismatic colourless crystals of 1. Yield: 41% based on Cd. Anal. Calc. for (C10H10N4O6Cl2Cd2): C, 20.78; H, 1.74; N, 9.69. Experimental: C, 20.84; H, 1.81; N, 9.87%. FT-IR (KBr pellet): 3396, 3097, 1618, 1596 1409cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; lithium chloride; In ethanol; water; for 4h;Inert atmosphere; Reflux; | General procedure: A sample of 0.0498 g (0.101 mmol)of Ru(dpop)Cl3(s) was mixed with 0.0248 g (0.157 mmol) of 2,20-bpy (excess), 0.3 g (7 mmol) LiCl and 1 ml Et3N in 75 ml of 95% ethanol/water and heated at reflux under Ar for 4 h. The mixture was cooled to room temperature then rotary evaporated to dryness. The crude solid was dissolved in a minimum volume of H2O and insoluble material removed by filtration. The filtrate was then loaded onto a Sephadex LH-20 chromatography column(20 cm height 3 cm diameter) and eluted with 0.10 M HCl(aq). Minor fractions eluted initially that were later identified by absorption spectroscopy as [Ru(dpop)2]+2 and [Ru(dpop)(bpy)(H2O)]+2. The largest [Ru(dpop)(bpy)Cl]+ fraction eluted last and was collected and rotary evaporated to dryness. The chromatographic and drying process was repeated a second time. Finally, the [Ru(dpop)(bpy)Cl]Cl(s) was dissolved in a minimumof CH3OH, and re-precipitated by addition of diethyl ether and collected by filtration. [Ru(dpop)(bpy)Cl]Cl(s) was converted to the PF6 salt by dissolution in a minimum volume of H2O, and addition of NH4PF6(s) to precipitate [Ru(dpop)(bpy)Cl]PF6(s). The solid was collected by filtration and washed with H2O to remove excess NH4PF6(s). After air drying overnight, the product was finally vacuum dried at 373 K giving 0.0269 g (0.0374 mmol) [Ru(dpop)(bpy)Cl]PF6(s); 37% yield Note: In some syntheses, the water soluble [Ru(dpop)(bpy)Cl]Cl(s) was retained for use in aquation studies. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With ammonium hydroxide; In ethanol; at 20℃; for 5h; | All the complexes of the type [Ln(tfaa)3]2bpm (where Ln = La, Eu and Tb) have been synthesized by a similar one step-one pot method (Scheme 1). The synthesis of [Eu(tfaa)3]2bpm described here is representative. A solution of Htfaa (0.25 g, 1.62 mmol) in ethanol (5 mL) was added to 0.12 mL (0.027 g, 1.62 mmol) 25% ammonia solution. This mixture, contained in a 50 mL beaker, was covered until the smell of ammonia disappeared. To this NH4tfaa solution were added 5 mL ethanol solutions of both bpm (0.0427 g, 0.27 mmol) and EuCl3*6H2O (0.1981 g, 0.54 mmol). The reaction mixture was stirred at room temperature for 5 h. A white precipitate of NH4Cl (which did not melt up to 300 C) appeared during stirring and this was filtered off repeatedly. The filtrate was covered and left for slow solvent evaporation at room temperature. A colourless powde rappeared after three days, which was filtered off and washed with CHCl3 several times. The product thus obtained was recrystallized twice from ethanol to get the pure compound and dried under vaccum over P4O10. A similar procedure was employed to synthesize the other complexes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With ammonium hydroxide; In ethanol; at 20℃; for 5h; | General procedure: All the complexes of the type [Ln(tfaa)3]2bpm (where Ln = La, Eu and Tb) have been synthesized by a similar one step-one pot method (Scheme 1). The synthesis of [Eu(tfaa)3]2bpm described here is representative. A solution of Htfaa (0.25 g, 1.62 mmol) in ethanol (5 mL) was added to 0.12 mL (0.027 g, 1.62 mmol) 25% ammonia solution. This mixture, contained in a 50 mL beaker, was covered until the smell of ammonia disappeared. To this NH4tfaa solution were added 5 mL ethanol solutions of both bpm (0.0427 g, 0.27 mmol) and EuCl3*6H2O (0.1981 g, 0.54 mmol). The reaction mixture was stirred at room temperature for 5 h. A white precipitate of NH4Cl (which did not melt up to 300 C) appeared during stirring and this was filtered off repeatedly. The filtrate was covered and left for slow solvent evaporation at room temperature. A colourless powde rappeared after three days, which was filtered off and washed with CHCl3 several times. The product thus obtained was recrystallized twice from ethanol to get the pure compound and dried under vaccum over P4O10. A similar procedure was employed to synthesize the other complexes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With ammonium hydroxide; In ethanol; at 20℃; for 5h; | General procedure: All the complexes of the type [Ln(tfaa)3]2bpm (where Ln = La, Eu and Tb) have been synthesized by a similar one step-one pot method (Scheme 1). The synthesis of [Eu(tfaa)3]2bpm described here is representative. A solution of Htfaa (0.25 g, 1.62 mmol) in ethanol (5 mL) was added to 0.12 mL (0.027 g, 1.62 mmol) 25% ammonia solution. This mixture, contained in a 50 mL beaker, was covered until the smell of ammonia disappeared. To this NH4tfaa solution were added 5 mL ethanol solutions of both bpm (0.0427 g, 0.27 mmol) and EuCl3*6H2O (0.1981 g, 0.54 mmol). The reaction mixture was stirred at room temperature for 5 h. A white precipitate of NH4Cl (which did not melt up to 300 C) appeared during stirring and this was filtered off repeatedly. The filtrate was covered and left for slow solvent evaporation at room temperature. A colourless powde rappeared after three days, which was filtered off and washed with CHCl3 several times. The product thus obtained was recrystallized twice from ethanol to get the pure compound and dried under vaccum over P4O10. A similar procedure was employed to synthesize the other complexes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | General procedure: cis-RuII(bpz)2Cl2 (100 mg, 0.205 mmol) and bpy (64 mg, 0.410 mmol) were combined in an argon-purged flask. An argon-sparged mixture of 2-methoxyethanol (7 mL) and water (3 mL) was added and the mixture heated at reflux for 24 h. After cooling to room temperature, the solvents were removed under vacuum and a small amount of water was added. The suspension was filtered, and an excess of solid NH4PF6 was added to the filtrate to precipitate the crude product. The solid was filtered off and purified by column chromatography on silica gel eluting with 0.1 M NH4PF6 in acetonitrile. The main orange fraction was evaporated to dryness and the product washed extensively with ice-cold water, then dried to give an orange solid. Yield: 95 mg (56%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; at 150℃; for 12h;High pressure; | General procedure: Lanza (for the chloride binuclear complex) [5a] and Jarabat (for the halide binuclear complexes) [5b] proposed a synthetic procedure consisting of mixing solutions of the inorganic salt and the organic ligand in water, ethanol or acetone (depending on the solubility of the salt) to obtain powder pure compounds. We decided to modify this methodology in order to obtain crystalline samples: (a) A solution of bpym (50mg, 0.32mmol) in 2mL of acetonitrile and a solution of HgX2 (X=Cl, Br, I, CN, SCN) (0.64mmol) in 20mL of acetonitrile were mixed, with the immediate formation of a precipitate (not relevant for the cyanide and chloride salts), and the yellow mixture obtained was refluxed for 2days, until the solution became orange and transparent. The solution was then concentrated at 25C and orange prismatic crystals were obtained and separated, which were suitable for X-ray analysis. For better crystals of 5, the initial small acicular crystalline product was redissolved in acetone at room temperature; after a week, prismatic orange crystals were obtained. (b) We also performed the synthesis of the various complexes under solvothermal conditions, with the previous quantity of reagents mixed in 100mL of acetonitrile. The reaction was performed at 150C for 12h, and after cooling gave the same crystalline phases as obtained with the first procedure. All the products have been analysed by powder X-ray diffraction and Raman spectroscopy to check their purity, and there are no relevant peaks of other phases or impurities. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; at 150℃; for 12h;High pressure; | General procedure: Lanza (for the chloride binuclear complex) [5a] and Jarabat (for the halide binuclear complexes) [5b] proposed a synthetic procedure consisting of mixing solutions of the inorganic salt and the organic ligand in water, ethanol or acetone (depending on the solubility of the salt) to obtain powder pure compounds. We decided to modify this methodology in order to obtain crystalline samples: (a) A solution of bpym (50mg, 0.32mmol) in 2mL of acetonitrile and a solution of HgX2 (X=Cl, Br, I, CN, SCN) (0.64mmol) in 20mL of acetonitrile were mixed, with the immediate formation of a precipitate (not relevant for the cyanide and chloride salts), and the yellow mixture obtained was refluxed for 2days, until the solution became orange and transparent. The solution was then concentrated at 25C and orange prismatic crystals were obtained and separated, which were suitable for X-ray analysis. For better crystals of 5, the initial small acicular crystalline product was redissolved in acetone at room temperature; after a week, prismatic orange crystals were obtained. (b) We also performed the synthesis of the various complexes under solvothermal conditions, with the previous quantity of reagents mixed in 100mL of acetonitrile. The reaction was performed at 150C for 12h, and after cooling gave the same crystalline phases as obtained with the first procedure. All the products have been analysed by powder X-ray diffraction and Raman spectroscopy to check their purity, and there are no relevant peaks of other phases or impurities. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; at 150℃; for 12h;High pressure; | General procedure: Lanza (for the chloride binuclear complex) [5a] and Jarabat (for the halide binuclear complexes) [5b] proposed a synthetic procedure consisting of mixing solutions of the inorganic salt and the organic ligand in water, ethanol or acetone (depending on the solubility of the salt) to obtain powder pure compounds. We decided to modify this methodology in order to obtain crystalline samples: (a) A solution of bpym (50mg, 0.32mmol) in 2mL of acetonitrile and a solution of HgX2 (X=Cl, Br, I, CN, SCN) (0.64mmol) in 20mL of acetonitrile were mixed, with the immediate formation of a precipitate (not relevant for the cyanide and chloride salts), and the yellow mixture obtained was refluxed for 2days, until the solution became orange and transparent. The solution was then concentrated at 25C and orange prismatic crystals were obtained and separated, which were suitable for X-ray analysis. For better crystals of 5, the initial small acicular crystalline product was redissolved in acetone at room temperature; after a week, prismatic orange crystals were obtained. (b) We also performed the synthesis of the various complexes under solvothermal conditions, with the previous quantity of reagents mixed in 100mL of acetonitrile. The reaction was performed at 150C for 12h, and after cooling gave the same crystalline phases as obtained with the first procedure. All the products have been analysed by powder X-ray diffraction and Raman spectroscopy to check their purity, and there are no relevant peaks of other phases or impurities. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; at 150℃; for 12h;High pressure; | General procedure: Lanza (for the chloride binuclear complex) [5a] and Jarabat (for the halide binuclear complexes) [5b] proposed a synthetic procedure consisting of mixing solutions of the inorganic salt and the organic ligand in water, ethanol or acetone (depending on the solubility of the salt) to obtain powder pure compounds. We decided to modify this methodology in order to obtain crystalline samples: (a) A solution of bpym (50mg, 0.32mmol) in 2mL of acetonitrile and a solution of HgX2 (X=Cl, Br, I, CN, SCN) (0.64mmol) in 20mL of acetonitrile were mixed, with the immediate formation of a precipitate (not relevant for the cyanide and chloride salts), and the yellow mixture obtained was refluxed for 2days, until the solution became orange and transparent. The solution was then concentrated at 25C and orange prismatic crystals were obtained and separated, which were suitable for X-ray analysis. For better crystals of 5, the initial small acicular crystalline product was redissolved in acetone at room temperature; after a week, prismatic orange crystals were obtained. (b) We also performed the synthesis of the various complexes under solvothermal conditions, with the previous quantity of reagents mixed in 100mL of acetonitrile. The reaction was performed at 150C for 12h, and after cooling gave the same crystalline phases as obtained with the first procedure. All the products have been analysed by powder X-ray diffraction and Raman spectroscopy to check their purity, and there are no relevant peaks of other phases or impurities. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; at 150℃; for 12h;High pressure; | General procedure: Lanza (for the chloride binuclear complex) [5a] and Jarabat (for the halide binuclear complexes) [5b] proposed a synthetic procedure consisting of mixing solutions of the inorganic salt and the organic ligand in water, ethanol or acetone (depending on the solubility of the salt) to obtain powder pure compounds. We decided to modify this methodology in order to obtain crystalline samples: (a) A solution of bpym (50mg, 0.32mmol) in 2mL of acetonitrile and a solution of HgX2 (X=Cl, Br, I, CN, SCN) (0.64mmol) in 20mL of acetonitrile were mixed, with the immediate formation of a precipitate (not relevant for the cyanide and chloride salts), and the yellow mixture obtained was refluxed for 2days, until the solution became orange and transparent. The solution was then concentrated at 25C and orange prismatic crystals were obtained and separated, which were suitable for X-ray analysis. For better crystals of 5, the initial small acicular crystalline product was redissolved in acetone at room temperature; after a week, prismatic orange crystals were obtained. (b) We also performed the synthesis of the various complexes under solvothermal conditions, with the previous quantity of reagents mixed in 100mL of acetonitrile. The reaction was performed at 150C for 12h, and after cooling gave the same crystalline phases as obtained with the first procedure. All the products have been analysed by powder X-ray diffraction and Raman spectroscopy to check their purity, and there are no relevant peaks of other phases or impurities. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55.8% | In tetrahydrofuran; methanol; water; at 20℃; | A solution of NiCl26H2O (95.2 mg, 0.401 mmol) in MeOH(5.0 mL) was slowly layered on top of an aqueous solution of THF(5.0 mL, middle) in a glass tube that contained 2,20-bipyrimidine(13.1 mg, 0.101 mmol) and trans-fumaric acid (11.7 mg,0.101 mmol). The green crystals of 1 were prepared after allowingthe solution to stand for several days at room temperature and isolatedon a filter, and dried in air. Yield: 55.8% (19.8 mg,0.0282 mmol) based on trans-fumaric acid. Anal. Calc. forC16H32N4Ni2O19: C, 27.38; H, 4.60; N, 7.98. Found: C, 27.38; H,4.22; N, 8.03. IR (KBr, cm-1): 3564w, 3070 s, 1558 s, 1417w,1384 s, 1225 m, 1207 s, 1148 m, 1115w, 1070 m, 1037 s, 986 s,801w, 757w, 687 s, 580w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.6% | In tetrahydrofuran; methanol; water; at 20℃; | General procedure: A solution of NiCl26H2O (95.2 mg, 0.401 mmol) in MeOH(5.0 mL) was slowly layered on top of an aqueous solution of THF(5.0 mL, middle) in a glass tube that contained 2,20-bipyrimidine(13.1 mg, 0.101 mmol) and trans-fumaric acid (11.7 mg,0.101 mmol). The green crystals of 1 were prepared after allowingthe solution to stand for several days at room temperature and isolatedon a filter, and dried in air. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.7% | In ethanol; at 20℃; for 6h; | All the reagents were obtained from Sigma Chemical Company (St. Louis, MO, USA) and used without further purification. The Cobalt(II) complex was prepared by direct reaction of ethanol solutions of sodium sulfaquinoxaline, 2,2?-bipyrimidine and CoCl2·6H2O in the 1:1:1M ratio under continuous stirring. The resulting solution was stirred during ca. 6h at room temperature and was then left to stand. Slow evaporation of the solution provided well-developed orange crystals that were suitable for X-ray diffraction. They were collected by filtration, washed, dried and subjected to elemental microanalyses. The elemental analysis (%) for C36H32CoN12O6S2 gave the following results: calc.: C, 50.76; H, 3.79; N, 19.73; S, 7.53; Found: C, 53.05; H, 3.75; N, 21.09; S, 7.76%. The yield was 78.7%. The stability of the complex was studied spectrophotometrically in aqueous solution at room temperature. No spectral changes were observed during a period of 24h (see Fig. S1 in the Supplementary information). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With hydrogenchloride; | To a solution of K4[WIV(CN)8]2H2O (0.2 mmol; 117 mg) and2,20-bipyrimidine (0.4 mmol; 64 mg) in 4 ml of water conc. HCl(130 ll) diluted in 0.5 ml of water was added. The red crystals of1 developed within minutes. The product was filtered and driedin the air. Yield: 50%. Anal. Calc. for C24H24N16O4W: C, 36.75; H,3.08; N, 28.57. Found: C, 36.57; H, 3.05; N, 28.11%. IR mCN:2116vs, 2160vs. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With potassium hydroxide; In water; N,N-dimethyl-formamide; | A mixture of H2hptz (0.3 mmol, 0.0486 g), copper(II) perchlorate hexahydrate (0.3 mmol, 0.111 g), and 2,2'-bipyrimidine (0.3 mmol, 0.0475 g) was dissolved in a solvent mixture of aqueous KOH (0.357 M, 2 mL) and DMF (2 mL) in a 10 mL vial. The solution color turned dark green, and it was then syringe filtered. The solution was then left to stand at room temperature for approximately 3 days, yielding dark green crystals (42% based on Cu2+). Anal. Calcd (Found) for C15H10N8OCu: C, 47.18(47.31); H, 2.64(2.85); N, 29.35(29.77). Selected IR data (cm-1, KBr pellet): 3074 (m, nu(C-H of hptz2-)), 1663 (m, nu(C=C of hptz2-)), 1601 (s, nu(C=C of bpym or hptz2-)), 1559 (s, nu(C=C of bpym and hptz2-)), 1506 (w, nu(hptz2-)), 1468 (s, nu(C=C of hptz2-)), 1432 (s, nu(bpym)), 1407 (s, nu(hptz2-)), 1311 (m, nu(hptz2-)), 1272 (m), 1251 (m), 1145 (m), 1101 (m, nu(hptz2-)), 1025 (w), 853 (m, nu(Cu-O and hptz2-)), 823 (w, nu(Cu-O and hptz2-)), 781 (s, nu(hptz2-)), 727 (m), 690 (m), 664 (m, nu(Cu-O)), 548 (m), 483 (m), 433 (w, nu(Cu-N)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium hydroxide; In water; N,N-dimethyl-formamide; | A mixture of H2hptz (0.3 mmol, 0.0486 g), zinc(II) perchlorate hexahydrate (0.3 mmol, 0.112 g), and 2,2'-bipyrimidine (0.3 mmol, 0.0475 g) was dissolved in a solvent mixture of aqueous KOH (0.357 M, 2 mL) and DMF (2 mL) in a 10 mL vial. The solution color changed to bright yellow, and the solution was then syringe filtered. The solution was then left to stand at room temperature for approximately 3 days, yielding yellow crystals (70% based on Zn2+). Anal. Calcd (Found) for C15H10N8OZn: C, 46.96(46.53); H, 2.63(2.89); N, 29.20(29.52). Selected IR data (cm-1, KBr pellet): 3080 (m, nu(C-H of hptz2-)), 1600 (s, nu(C=C of bpym or hptz2-)), 1558 (s, nu(C=C of bpym and hptz2-)), 1504 (w, nu(hptz2-)), 1465 (s, nu(C=C of hptz2-)), 1431 (s, nu(bpym)), 1408 (s, nu(hptz2-)), 1338 (m, nu(hptz2-)), 1293 (m), 1257 (m), 1211 (m) 1163 (m), 1107 (m, nu(hptz2-)), 1031 (w), 869 (m, nu(Zn-O and hptz2-)), 822 (w, nu(Zn-O and hptz2-)), 785 (s, nu(hptz2-)), 733 (m), 689 (m), 657 (m, nu(Zn-O)), 627 (m), 586 (m), 568 (w, nu(Zn-N)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In water; N,N-dimethyl-formamide; | A mixture of H2hptz (0.3 mmol, 0.0486 g), nickel(II) perchloratehexahydrate (0.3 mmol, 0.110 g) and 2,20-bipyrimidine (0.6 mmol,0.0949 g) was dissolved in a solvent mixture of aqueous KOH(0.357 M, 2 mL) and DMF (2 mL) in 10 mL vial. The solution turned bright brown and was then syringe filtered. The solution was left tostand at room temperature for approximately 3 days, yieldingbright brown crystals (55% based on Ni2+).Anal. Calcd. (Found) for C23H16KN12NiO5.5: C, 42.75(41.77); H,2.50(2.70); N, 26.01(26.88).Selected IR data (cm-1, KBr pellet): 3458 (s, br, m(O-H;H2O),3090 (m, m(C-H of hptz2)), 1629 (m, m(CC of hptz2)), 1596 (s,m(CC of bpym or hptz2)), 1557 (s, m(CC of bpym and hptz2)),1470 (w, m(hptz2)), 1403(s, m(CC of hptz2)), 1376 (s, m(bpym)),1326 (s, m(hptz2)), 1271 (m, m(hptz2)), 1252 (m), 1210 (m),1144 (m), 1111 (m, m(hptz2)), 1092 (w), 1010 (s), 850 (m, m(Ni-O and hptz2)), 823 (w, m(Ni-O and hptz2)), 773 (s, m(hptz2)),760 (m), 725 (s), 687 (m), 659 (m, m(Ni-O)), 568 (m), 489 (m),442 (w, m(Ni-N)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 8h;Reflux; | 200mg [IrCp*Cl2]2 Ethanol solution was treated with 79mg 2,2'-bipyrimidyl in a 25mL round-bottomed flask. The mixture solution was stirred and heated under reflux for 8 hours. The insoluble [IrCp*Cl2]2 would dissolve and the solution turned pale yellow during the reflux. Yellow product could be gained after removing the ethanol by rotary distillation under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With ammonium hydroxide; In ethanol; at 20℃; for 5h; | General procedure: A solution of Htfaa (1.0g, 6.48mmol) in ethanol (5mL) was added to a 0.48mL (0.108g, 6.48mmol) 25% ammonia solution. This mixture was covered in 50mL beaker until all the ammonia vapors dissolved. To this mixture was added a 5mL ethanol solution of bpy (0.3371g, 2.16mmol) and a 5mL ethanol solution of SmCl3·6H2O (0.7879g, 2.16mmol). The reaction mixture was stirred at room temperature for 5h. A white precipitate of NH4Cl (which does not melt up to 300C) appeared during stirring, which was filtered off repeatedly. The filtrate was covered and left for slow solvent evaporation at room temperature. A powder appeared after three days, which was filtered off and washed with CHCl3 several times. The product thus obtained was recrystallized twice from ethanol to get the pure compound and dried under vacuum over P4O10. A similar method was used to synthesize [Sm(tfaa)3phen]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | General procedure: Under a N2 atmosphere, [(CH3CN)4Cu]BF4 (1.0 equiv) and theorganic phosphine ligand (2.0 equiv for PPh3 and TPA-PPP; 1.0equiv for DPEPHOS and XANTPHOS) were mixed in CH2Cl2. Afterstirring for 2 h at room temperature, the corresponding 2,2'-bipyrimidine-based ligand (0.5 equiv) was added. The reaction wasallowed to proceed at room temperature for 4 h. The solvent wasremoved under reduced pressure. The colored residue was dissolvedin CH2Cl2 (2 mL) and precipitated in diethyl ether. Theprecipitation was collected by filtration and washed with diethylether three times. The title Cu(I) complexes were obtained ascolored solids in high yields. 2.4.6.1. Cu-MD-1 [24](yield: 94%) 1H NMR (400 MHz, CDCl3). delta (ppm) 8.74 (d, J 5.2 Hz, 4H), 7.91 (t, J 5.2 Hz, 2H), 7.31 (t,J 7.2 Hz, 12H), 7.15 (t, J 7.2 Hz, 24H), 7.06 (br, 24H); 31P NMR(162 MHz, CDCl3): delta (ppm) 3.81 (s); FAB-MS (m/z): 1332 [M-2BF4]+;Anal. Calcd. for C80H66B2Cu2F8N4P4: C, 63.72; H, 4.41; N, 3.72;found: C, 63.53; H, 4.48; N, 3.63. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | General procedure: Under a N2 atmosphere, [(CH3CN)4Cu]BF4 (1.0 equiv) and theorganic phosphine ligand (2.0 equiv for PPh3 and TPA-PPP; 1.0equiv for DPEPHOS and XANTPHOS) were mixed in CH2Cl2. Afterstirring for 2 h at room temperature, the corresponding 2,2'-bipyrimidine-based ligand (0.5 equiv) was added. The reaction wasallowed to proceed at room temperature for 4 h. The solvent wasremoved under reduced pressure. The colored residue was dissolvedin CH2Cl2 (2 mL) and precipitated in diethyl ether. Theprecipitation was collected by filtration and washed with diethylether three times. The title Cu(I) complexes were obtained ascolored solids in high yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | General procedure: Under a N2 atmosphere, [(CH3CN)4Cu]BF4 (1.0 equiv) and theorganic phosphine ligand (2.0 equiv for PPh3 and TPA-PPP; 1.0equiv for DPEPHOS and XANTPHOS) were mixed in CH2Cl2. Afterstirring for 2 h at room temperature, the corresponding 2,2'-bipyrimidine-based ligand (0.5 equiv) was added. The reaction wasallowed to proceed at room temperature for 4 h. The solvent wasremoved under reduced pressure. The colored residue was dissolvedin CH2Cl2 (2 mL) and precipitated in diethyl ether. Theprecipitation was collected by filtration and washed with diethylether three times. The title Cu(I) complexes were obtained ascolored solids in high yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | General procedure: Under a N2 atmosphere, [(CH3CN)4Cu]BF4 (1.0 equiv) and theorganic phosphine ligand (2.0 equiv for PPh3 and TPA-PPP; 1.0equiv for DPEPHOS and XANTPHOS) were mixed in CH2Cl2. Afterstirring for 2 h at room temperature, the corresponding 2,2'-bipyrimidine-based ligand (0.5 equiv) was added. The reaction wasallowed to proceed at room temperature for 4 h. The solvent wasremoved under reduced pressure. The colored residue was dissolvedin CH2Cl2 (2 mL) and precipitated in diethyl ether. Theprecipitation was collected by filtration and washed with diethylether three times. The title Cu(I) complexes were obtained ascolored solids in high yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20℃; for 5h; | The molar ratio of[RuII(bpy)2(H2O)2]SO4 to 2,2'-bipyrimidine wasabout 1 : 1 in H2O, the mixture was stirred at ambienttemperature for 5 h and chromatographed on a Sephadex SephadexG-10 column using H2O as an eluent. The productwas evaporated under reduced pressure to yield anorange powder of [RuII(bpy)2(bpm)]SO4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In chloroform; at 20℃; for 0.25h; | 0.013 g (0.085 mmol) of 2, 20-bipyrimidine were added to a solutionof cis-[Pt(C6F5)2(thf)2] (0.115 g, 0.171 mmol) in 15 ml of CHCl3.Instantaneously, a solid precipitated and the suspension was stirred at room temperature for 15 min. Then the solution was evaporated to 5mL approximately, and the resulting dark orange solid was filtered off and washed with n-hexane. (91% yield). Anal. Found(Calcd. for C32H6N4F20Pt2): C, 31.31 (31.59); H, 0.72 (0.50); N, 4.80(4.60). IR (cm-1): C6F5 X-sensitive mode [44] 815 s, 806 s; other,nu(C-F), 965 s; C8H6N4, 1586 w, 1557 m, 1503 s, 1419 m, 754 m; 1HNMR (room temperature), d6-acetone; delta/ppm: 9.34 ppm(d, 4H),8.34 ppm (t, 2H). 19F NMR (room temperature), d6-acetone(282.231 MHz); delta/ppm: 114.93 (d, 4Fo, 3J=Pt-Fo 459.82 Hz), 115.01(d, 4Fo, 3J=Pt-Fo 460.95 Hz), 158.50 (t, 4Fp, 4J=Fp-Fo 38.65 Hz), 161.00 (m, 8Fm). FAB+ (m/z): [Pt2(C6F5)4(C8H6N4)]:1216. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 4.0h;Heating; | General procedure: The complexes, [{Ln(acac)3}2(l-bpm)] (Ln = Nd (1c) and Eu(2c)) were prepared following the procedure described by Ilmiet al., with some modification [10]. To a mixture of 2,20-bipyrimidine,bpm (0.50 mmol) and <strong>[18115-70-3]lithium acetylacetonate</strong>, <strong>[18115-70-3]Li(acac)</strong>(3.00 mmol) in absolute EtOH (20 mL) was added an absolute EtOHsolution (10 mL) of LnCl36H2O (1.00 mmol) (Ln = Nd or Eu). Themixture was stirred on a hot plate at an elevated temperaturebelow the boiling point of the solvent for 4 h and the resultingsolution (concentrated to ca. 15 mL) was filtered. The filtrate waskept at room temperature for slow evaporation of the solvent. Single-crystals suitable for X-ray diffraction study were obtainedwithin 24 h. The crystals were collected by filtration and dried inair. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With [2,2]bipyridinyl; 1,10-Phenanthroline; In methanol; at 20℃; for 4h; | General procedure: The complexes were prepared by a similar procedure(Scheme 1) as that for the mononuclear 2,2'-bipyridine (bpy) and1,10-phenanthroline (phen) complexes [17]. To a mixture of 2,2'-bipyrimidine, bpm (1.00 mmol) and sodium dimethyldithiocarbamate,Na(Me2dtc) or ammonium pyrrolidine dithiocarbamate,NH4(pyrdtc) (3.00 mmol) in MeOH (20 mL) was added a methanolsolution (10 mL) of LnCl36H2O (Ln = Nd or Eu) (1.00 mmol). Themixture was stirred for 4 h at room temperature and the resultingprecipitate was collected by filtration, washed with MeOH anddried in air. The crude product was purified by recrystallization.The method of recrystallization, the results of elemental analysisand the FT-IR spectral data of the respective complexes are givenbelow. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With [2,2]bipyridinyl; 1,10-Phenanthroline; In methanol; at 20℃; for 4h; | General procedure: The complexes were prepared by a similar procedure(Scheme 1) as that for the mononuclear 2,2'-bipyridine (bpy) and1,10-phenanthroline (phen) complexes [17]. To a mixture of 2,2'-bipyrimidine, bpm (1.00 mmol) and sodium dimethyldithiocarbamate,Na(Me2dtc) or ammonium pyrrolidine dithiocarbamate,NH4(pyrdtc) (3.00 mmol) in MeOH (20 mL) was added a methanolsolution (10 mL) of LnCl36H2O (Ln = Nd or Eu) (1.00 mmol). Themixture was stirred for 4 h at room temperature and the resultingprecipitate was collected by filtration, washed with MeOH anddried in air. The crude product was purified by recrystallization.The method of recrystallization, the results of elemental analysisand the FT-IR spectral data of the respective complexes are givenbelow. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 4.0h;Heating; | General procedure: The complexes, [{Ln(acac)3}2(l-bpm)] (Ln = Nd (1c) and Eu(2c)) were prepared following the procedure described by Ilmiet al., with some modification [10]. To a mixture of 2,20-bipyrimidine,bpm (0.50 mmol) and <strong>[18115-70-3]lithium acetylacetonate</strong>, <strong>[18115-70-3]Li(acac)</strong>(3.00 mmol) in absolute EtOH (20 mL) was added an absolute EtOHsolution (10 mL) of LnCl36H2O (1.00 mmol) (Ln = Nd or Eu). Themixture was stirred on a hot plate at an elevated temperaturebelow the boiling point of the solvent for 4 h and the resultingsolution (concentrated to ca. 15 mL) was filtered. The filtrate waskept at room temperature for slow evaporation of the solvent. Single-crystals suitable for X-ray diffraction study were obtainedwithin 24 h. The crystals were collected by filtration and dried inair. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With [2,2]bipyridinyl; 1,10-Phenanthroline; In methanol; at 20℃; for 4h; | General procedure: The complexes were prepared by a similar procedure(Scheme 1) as that for the mononuclear 2,2'-bipyridine (bpy) and1,10-phenanthroline (phen) complexes [17]. To a mixture of 2,2'-bipyrimidine, bpm (1.00 mmol) and sodium dimethyldithiocarbamate,Na(Me2dtc) or ammonium pyrrolidine dithiocarbamate,NH4(pyrdtc) (3.00 mmol) in MeOH (20 mL) was added a methanolsolution (10 mL) of LnCl36H2O (Ln = Nd or Eu) (1.00 mmol). Themixture was stirred for 4 h at room temperature and the resultingprecipitate was collected by filtration, washed with MeOH anddried in air. The crude product was purified by recrystallization.The method of recrystallization, the results of elemental analysisand the FT-IR spectral data of the respective complexes are givenbelow. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With [2,2]bipyridinyl; 1,10-Phenanthroline; In methanol; at 20℃; for 4h; | General procedure: The complexes were prepared by a similar procedure(Scheme 1) as that for the mononuclear 2,2'-bipyridine (bpy) and1,10-phenanthroline (phen) complexes [17]. To a mixture of 2,2'-bipyrimidine, bpm (1.00 mmol) and sodium dimethyldithiocarbamate,Na(Me2dtc) or ammonium pyrrolidine dithiocarbamate,NH4(pyrdtc) (3.00 mmol) in MeOH (20 mL) was added a methanolsolution (10 mL) of LnCl36H2O (Ln = Nd or Eu) (1.00 mmol). Themixture was stirred for 4 h at room temperature and the resultingprecipitate was collected by filtration, washed with MeOH anddried in air. The crude product was purified by recrystallization.The method of recrystallization, the results of elemental analysisand the FT-IR spectral data of the respective complexes are givenbelow. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In methanol; at 20℃; for 4h;Inert atmosphere; Schlenk technique; | A mixture of 122.0mg (0.2 mmol) of the dichloro(mu6-p-cymene)Ru(II) dimer, 31.6mg(0.2 mmol) of 2,2'-bipyrimidine and 77.0mg (0.42 mmol) of KPF6 in 20 mL methanolwas stirred at room temperature for 4 h to form a yellow precipitate. The precipitate was filtered off, washed with (310 mL) diethyl ether and dried under vacuum.Crystals of the complex were grown by slow diffusion of diethyl ether into an acetonic solution of the complex. Yield: (118.8 mg, 60%). Anal. Calcd for C28H34Cl2N4P2F12Ru2(%): C, 34.0; H, 3.5; N, 5.7. Found: C, 34.2; H, 3.8; N, 5.4. 1H NMR (500 MHz, acetone-d6),delta (ppm): 10.15 (d, 4 H, CHpyridyl), 8.40 (t, 2 H, CHpyridyl), 6.49 (d, 4 H, CHp-cymene), 6.26 (d,4H, CHp-cymene), 2.89 (hept, 2H, CHp-cymene), 2.36 (s, 6H, CH3) and 1.14 (d, 12 H,CH(CH3)2). 13C NMR (500 MHz, acetone-d6), delta (ppm): 163.8, 161.6, 126.9, 108.4, 105.2,85.8, 84.1, 31.1, 21.5, 18.1. MS (TOF, ESI) (m/z): 429.05 [mu6-p-cymene RuClbipyrimidyl], 270.99 [mu6-p-cymene-RuCl]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; acetic acid; at 50℃; for 4h; | To a solution of 2,2?-bipyrimidine (5 g, 31.6 mmol) in glacial acetic acid (30 mL) was added bromine (1.95 mL, 37.9 mmol) and the reaction was stirred at 50 oC for 4 hours. The solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 (50 mL), neutralized with saturated aqueous NaHCO3 solution (50 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by normal phase SiO2 chromatography (0% to 5% MeOH/CH2Cl2) to afford a mixture of 5-bromo-2-pyrimidin-2- yl-pyrimidine and 4-bromo-2-pyrimidin-2-yl-pyrimidine as a light brown solid, which was used without further purification (6.1 g, 67 % yield). |
Tags: 34671-83-5 synthesis path| 34671-83-5 SDS| 34671-83-5 COA| 34671-83-5 purity| 34671-83-5 application| 34671-83-5 NMR| 34671-83-5 COA| 34671-83-5 structure
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