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[ CAS No. 2915-16-4 ] {[proInfo.proName]}

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Chemical Structure| 2915-16-4
Chemical Structure| 2915-16-4
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Product Details of [ 2915-16-4 ]

CAS No. :2915-16-4 MDL No. :MFCD00030776
Formula : C16H11ClN2 Boiling Point : -
Linear Structure Formula :N2C4HClC6H5C6H5 InChI Key :QNGVEVOZKYHNGL-UHFFFAOYSA-N
M.W : 266.73 Pubchem ID :1804739
Synonyms :

Calculated chemistry of [ 2915-16-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 77.91
TPSA : 25.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.05
Log Po/w (XLOGP3) : 4.49
Log Po/w (WLOGP) : 4.46
Log Po/w (MLOGP) : 3.21
Log Po/w (SILICOS-IT) : 4.63
Consensus Log Po/w : 3.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.89
Solubility : 0.00342 mg/ml ; 0.0000128 mol/l
Class : Moderately soluble
Log S (Ali) : -4.75
Solubility : 0.00472 mg/ml ; 0.0000177 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.3
Solubility : 0.0000132 mg/ml ; 0.0000000497 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 2915-16-4 ]

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

Application In Synthesis of [ 2915-16-4 ]

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

  • Upstream synthesis route of [ 2915-16-4 ]
  • Downstream synthetic route of [ 2915-16-4 ]

[ 2915-16-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 3764-01-0 ]
  • [ 98-80-6 ]
  • [ 2915-16-4 ]
YieldReaction ConditionsOperation in experiment
86% With sodium carbonate In ethanol; toluene at 120℃; for 3 h; Preparation of Compound 1-10 [113] 2,4,6-trichloropyrimidine (20 g, 0.109 mol), phenylboronic acid (29.2 g, 0.239 mol), Pd(PPh3)4 (6.3 g, 0.005 mol), Na2CO3(2M) (163 mL) and EtOH (163 mL) were dissolved in toluen (320 mL) and the mixture was heated at 120 . When the reaction was completed after stirring the mixture for 3 hours, the reaction mixture was washed with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-10 (25 g, 86percent) was obtained through purification by column chromatography.
76.9% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane for 8 h; Reflux; Inert atmosphere In a 500 mL three-necked flask under argon atmosphere, 2,4,6-trichloropyrimidine (5 g, 27.3 mmol), phenylboronic acid (6.7 g, 54.9 mmol), tetrakistriphenylphosphine palladium (1.26 g, 1.09 mmol ), Dimethoxyethane (DME, 100 mL) and a 2M sodium carbonate aqueous solution (82 mL, 164 mmol) were added, and the mixture was reacted for 8 hours while heating and refluxing. After the reaction solution was cooled to room temperature, the aqueous layer was separated and the organic layer was dried over magnesium sulfate. The insoluble material was removed by filtration, and the organic solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate (a) (5.6 g, yield 76.9percent).
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene for 8 h; Reflux; Inert atmosphere Take 5000ml three necked flask, equipped with mechanical stirrer, condenser. Feed: 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182,0.10 mol), phenylboronic acid 28.1 g (molecular weight 122,0.23 mol), tetrakis(triphenylphosphine)palladium 12.0g (0.0104mol), potassium carbonate 60 g (0.435 mol), tetrahydrofuran 600 ml, toluene 400 ml, water 400 ml. Mechanical agitation was initiated under conditions of reduced pressure ventilation Ar gas three times to maintain protection, monitoring the reaction by TLC (thin layer chromatography), refluxed for 8 hours, the reaction was complete. Allowed to cool, the reaction system was divided into two layers, the organic layer was separated and evaporated to dryness to give a solid product, which was recrystallized from toluene to give intermediate M3-1 was 19.9 g, molecular weight 266, 75percent yield.
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene for 8 h; Reflux; Inert atmosphere Under the protection of Ar gas, in 500mL three-neck bottle added 2,4,6- Trichloropyrimidine18.2g(molecular weight 182,0.10mol), Benzene boronic acid 28. 1g (molecularweight 122,0 · 23 mol), Tetrakis (triphenylphosphine) palladium12.0g(0.0104mol), 600ml of THF, 400mL toluene, Potassium carbonate 60g (0 · 435mol) was dissolved in 400ml water and the formation of solution was added intoreaction flask. After repeated ventilation under reduced pressure, startelectric mixer, the reaction was monitored by TLC (thin layer chromatography),after at reflux for 8h and the reaction was complete. Allowed to cool, thereaction system was divided into two layers, the organic layer was separatedand evaporated to dryness to give a solid product, it was recrystallized using toluene to give 19.9gof intermediate molecular weight of 266, yield of 75percent.
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene for 8 h; Inert atmosphere; Reflux Under Ar protection, in a 5000ml three-necked flask was added 2,4,6_ trichloropyrimidine 18.2g (molecular weight 182,0.1Omol), benzene boronic acid 28.1g (molecular weight 122,0.23mol ), tetrakis (triphenylphosphine) palladium 12.0g (0.0104mol), 600ml ^ THF, 400ml of toluene, potassium carbonate 60g (0.435mol) dissolved in 400ml of water was added to the reaction flask.After refluxed for 8 hours, repeated under reduced pressure ventilation, electric start stirring, the reaction was monitored by TLC (thin layer chromatography), the reaction was complete.Allowed to cool, the reaction system was divided into the second floor, and the organic layer was separated, evaporated to dryness, to obtain a solid product, which was recrystallized from toluene to give 19.9g of intermediate molecular weight 266, 75percent yield.
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene for 8 h; Reflux; Inert atmosphere M2-1: under Ar protection, a 5000ml three-necked flask were added 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182,0.10mol), phenylboronic acid 28.1 g (molecular weight 122,0.23mol), four (triphenylphosphine) palladium 12.0g (0.0104mol), 600ml of THF to, toluene 400ml, potassium carbonate 60g (0.435mol) dissolved in 400ml of water was added to form a reaction flask. After repeated under reduced pressure ventilation, electric start stirring, the reaction was monitored by TLC (thin layer chromatography), refluxed for 8 hours, the reaction was complete. Allowed to cool, the reaction system for the sub-floor, the organic layer was separated, evaporated to dryness to give a solid product, recrystallised from toluene to give 19.9g intermediate molecular weight 266, 75percent yield.
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene for 8 h; Inert atmosphere; Reflux Take 5000ml three bottles, with mechanical mixing, condenser. Feeding: 2,4.6-trichloropyrimidine (molecular weight: 182,010 mol), 28.1 g of benzene boronic acid (molecular weight: 122, 0.23 mol), 12.0 g (0.0104 mol) of tetraphenylphenylphosphine, 60 g of potassium carbonate (0.435 mol ), Tetrahydrofuran 600ml, toluene 400ml, water 400ml. start mechanical agitation, Under the conditions of reduced pressure ventilation 3 times to maintain Ar gas protection, with TLC (thin layer chromatography) to monitor the reaction, After 8 hours of reflux, the reaction was complete. Let cool, the reaction body divided into two layers, separated from the organic layer, evaporated, The solid product was obtained and recrystallized from toluene to give 19.9 g of intermediate M2-1, molecule The amount of 266, the yield of 75percent.
74% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 8 h; Inert atmosphere A mixture of 2, 4, 6-trichloropyrimidine (PYR, 1.3 ml, 7 mmol),phenylboronic acid (Ph-BoA, 1.5 g, 12 mmol), Pd(PPh3P)4 (0.2 g,0.17 mmol), 40 ml of 2M aqueous K2CO3 solution, 40 ml of water, 25 mlof ethanol, and 80 ml of toluene were added in a two neck round bottom flask equipped with condenser and refluxed at 110 °C for 8 h under nitrogen atmosphere. After completion of the reaction, the mixture was worked up using ethyl acetate (60 ml) and water (50 ml). The organic layer was dried over anhydrous magnesium sulfate and then filtered and concentrated. The crude residues were separated using asilica column and an n-hexane: dichloromethane (4:1) solvent system toobtain the intermediate 2P-PYR as a white solid. 2.3.2.1. 2-Chloro-4, 6-diphenylpyrimidine. Yield: 74percent; white solid; 1HNMR (500 MHz, CDCl3) δ 8.13–8.14 (m, 4H), 8.01 (s, 1H), 7.51–7.55(m, 6H); 13C NMR (500 MHz, CDCl3) δ 167.7, 162.1, 135.7, 131.7,129.1, 127.5, 111.0.
70% With sodium carbonate In 1,2-dimethoxyethane; water for 15 h; Inert atmosphere; Reflux Under an Ar gas atmosphere, 2,4,6-trichloropyrimidine (18.3 g, 100 mmol), phenylboronic acid (24.4 g, 200 mmol), palladium acetate (0.56 g, 2.5 mmol), triphenylphosphine (1.31 g, 5.0 mmol), DME (930 ml) and an aqueous solution of 2M sodium carbonate (310 ml) were stirred for 15 hours at a reflux temperature. The solvent was distilled away under reduced pressure. The obtained residue was extracted by dichloromethane. The residue obtained by concentrating the organic phase was refined by silica-gel column chromatography (a developing solvent: hexane-ethyl acetate) to provide an intermediate body X1 as a white solid. A yield of the intermediate body X1 was 18.7 g and a yield rate thereof was 70percent. (reference document : J.Org.Chem. 66 7125-7128 (2001))
69% With sodium carbonate In ethanol; water; toluene at 120℃; for 2 h; After 2,4,6-nichluropyiimidin 25g(l 362mm 1), phenylbu x n c acid 36.5g(299.3mmol), and tetrakis(triphenyLphosp}tine)palladium (1.118 Q96mmoL) were dissolved in toluene (408mL), 2.OM Na,CA, aqueous solution (204 mL) and ethanol (204mL) were added thereto. The mixture was stored under influx for 2 hours at 120C. Upon completion of the reaction, extraction with EA and purification by column chromatography gave a compound 1-2 (25g, 93.7mmol, 69percent).
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; waterReflux The starting material, 2,4,6-trichloropyrimidine (60 g, 327 mmol) to THF (2878 mL) to dissolve after phenylboronic acid (79.8 g, 654 mmol), Pd (PPh3) 4 (22.7 g, 19.6 mmol), K2CO3 (271 g, 1962 mmol), followed by the addition of water (1440 mL), stirred and refluxed. When the reaction is complete, the ether was extracted with water, the organic layer was concentrated after then, the resulting organic was dried over MgSO4 and concentrated to silicagel column and recrystallization. To obtain the product 53.9 (Yield: 68percent)
63% With sodium carbonate In 1,2-dimethoxyethane; water for 8 h; Inert atmosphere; Reflux Synthesis Example 1 (Synthesis of Compound 1); Under a nitrogen atmosphere, trichloropyrimidine (10 g, 54.5 mmol), phenylboronic acid (13.3 g, 109 mmol), palladium acetate (0.3 g, 1.37 mmol), triphenylphosphine (0.72 g, 2.73 mmol), dimethoxyethane (150 mL) and an aqueous solution of 2M sodium carbonate (170 mL) were added together in sequential order, and heated to reflux for 8 hours. After the reaction solution was cooled down to the room temperature, an organic layer was removed and an organic solvent was distilled away under reduced pressure. The obtained residue was refined by silica-gel column chromatography, whereby an intermediate body 1-1 (9.2g, a yield of 63percent) was obtained.
63% With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 8 h; Reflux; Inert atmosphere Under a nitrogen atmosphere, trichloropyrimidine (10 g, 54.5 mmol), phenylboronic acid (13.3 g, 109 mmol), palladium acetate (0.3 g, 1.37 mmol), triphenylphosphine (0.72 g, 2.73 mmol), dimethoxyethane (150 mL) and an aqueous solution of 2M sodium carbonate (170 mL) were added together in sequential order, and heated to reflux for eight hours. -After the reaction solution was cooled down to the room temperature, an organic phase was removed and an organic solvent was distilled away under reduced pressure. The obtained residue was refined by silica-gel column chromatography, whereby an intermediate 5-1 (9.2 g, a yield of 63percent) was obtained.
63% With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 8 h; Inert atmosphere; Reflux Under a nitrogen atmosphere, trichloropyrimidine (10 g, 54.5 mmol), phenylboronic acid (13.3 g, 109 mmol), palladium acetate (0.3 g, 1.37 mmol), triphenylphosphine (0.72 g, 2.73 mmol), dimethoxyethane (150 mL) and an aqueous solution of 2M sodium carbonate (170 mL) were added together in sequential order, and heated to reflux for 8 hours. After the reaction solution was cooled down to the room temperature, an organic layer was removed and an organic solvent was distilled away under reduced pressure. The obtained residue was refined by silica-gel column chromatography, whereby an intermediate body 2H-1 (9.2 g, a yield of 63percent) was obtained
58% With sodium carbonate In ethanol; water; toluene at 80℃; for 3 h; Preparation of Compound G [72] 2,4,6-trichloropyrimidine (16.8 g, 91 mmol), phenylboronic acid (24.4 g, 200 mmol), Pd(PPh3)4 (5.3 g, 4.6 mmol), and Na2CO3 (29 g, 273 mmol) were added in a RBF. Toluene (350 mL), EtOH (100 mL), and H2O (150 mL) were added to the mixture. The reaction mixture was stirred at 80 for 3 hours and extracted with EA/H2O. After removing moisture with MgSO4 and performing distillation under reduced pressure, Compound G (14 g, 58percent) was obtained by column separation under the condition of MC:Hexane=1:10.
48.14% With potassium carbonate In ethanol; toluene for 4 h; Reflux 2,4,6-trichloropyrimidin (10g, 54.51mmol), phenylboronic acid (16.6g, 136,29mmol), Pd(PPh3)4 (3.15g, 2.72mmol), 2M K2CO3 (50ml), toluene (100ml) and ethanol (30ml)were mixed and stirred under reflux. 4 hours later, the mixture was cooled room temperature, distilled water was added. After extracting with EA and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 2-1 (7g, 26.24mmol, 48.14percent).
48% With potassium carbonate In ethanol; toluene for 4 h; Reflux Preparation of Compound 1-4 2,4,6-trichloropyrimidine (10 g, 54.51 mmol), phenylboronic acid (16.6 g, 136,29 mmol), Pd(PPh3)4 (3.15 g, 2.72 mmol), 2M K2CO3 (50 mL), toluen (100 mL) and ethanol (30 mL) were stirred under reflux. 4 hours later, the mixture was cooled to room temperature and extracted with EA after adding distilled water. After drying with MgSO4 and distillation under reduced pressure, Compound 1-4 (7 g, 48.percent) was obtained by column separation.
41% With sodium carbonate In 1,2-dimethoxyethane; water at 70℃; for 24 h; Example 89; 2-Chloro-4 , 6-diphenylpyrimidine; A mixture of 2, 4, 6-trichloropyrimidine, 2.76g (15.0 mmol) , phenylboronic acid, 3.66g (30.0 mmol) , Pd(OAc)2, 86mg (0.38 mmol), triphenylphosphine, 200mg (0.76 mmol) in 15OmL of ethylene glycol dimethyl ether was heated to obtain a clear solution. To the solution was added 25mL of 4.0M aq. Na2CO3. The reaction mixture was refluxed for 24h at 70 °C. The mixture was cooled to room temperature and diluted with 10OmL ethyl acetate. The organic layer was washed with water, sat. aq. NaCl, and dried (MgSO4) . After the solution was concentrated, the residue was recrystallized with Et2ψ-Heptane (1:3) to afford the desired product in 1.64g (41percent) as a pale yellow solid.
41% With sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 70℃; for 24 h; mixture of 2,4, 6-Trichloropyrimidine, 2.76g (15.0 mmol), phenylboronic acid, 3. 66G (30. 0 mmol), Pd (OAc) 2, 86MG (0. 38 mmol), triphenylphosphine, 200mg (0.76 mmol) in 150ML of ethylene glycol dimethyl ether was heated to obtain a clear solution. To the solution was added 25mL of 4. OM aq. NA2CO3. The reaction mixture was refluxed for 24h at 70 °C. The mixture was cooled to room temperature and diluted with 100mL ethyl acetate. The organic layer was washed with water (2X50ML), sat. aq. NaCl (LX50ML), and dried (MGS04). After the solution was concentrated, the residue was recrystallized with ET2O-HEPTANE (1: 3) to afford the desired product in 1.64g (41percent) as a pale yellow SOLID. 1H NMR (CDC13): 5 8.15-8. 12 (m, 4H), 8.02 (s, 1H), 7.57-7. 51 (m, 6H).
41% With sodium carbonate In 1,2-dimethoxyethane; water at 70℃; for 24 h; A mixture of 2,4, 6-trichloropyrimidine, 2.76g (15.0 mmol), phenylboronic acid, 3.66g (30.0 mmol), Pd (OAc) 2, 86mg (0.38 mmol), triphenylphosphine, 200mg (0.76 mmol) in 150ML of ethylene glycol dimethyl ether was heated to obtain a clear solution. To the solution was added 25mL of 4. OM aq. NA2CO3. The reaction mixture was refluxed for 24h at 70 °C. The mixture was cooled to room temperature and diluted with LOOML ethyl acetate. The organic layer was washed with water, sat. aq. NaCl, and dried (MgS04). After the solution was concentrated, the residue was recrystallized with Et20-Heptane (1: 3) to afford the desired product in 1.64g (41percent) as a pale yellow SOLID. 1H NMR (CDC13) 8. 15-8. 12 (m, 4H), 8. 02 (s, 1H), 7.57-7. 51 (m, 6H).
38% With palladium diacetate; sodium hydrogencarbonate; tris-(o-tolyl)phosphine In 1,2-dimethoxyethane for 16 h; Reflux 2-Chloro-4,6-diphenylpyrimidine
750 g (0.41 mmol) of 1,3,5-trichloropyrimidine, 100 g (0.82 mol) of phenylboronic acid and 625 ml of 4 M NaHCO3 solution are suspended in 2.5 l of ethylene glycol dimethyl ether. 2.3 g (10.23 mmol) of Pd(OAc)2 and 10.35 g (34 mmol) of P(o-Tol)3 are added to this suspension, and the reaction mixture is heated under reflux for 16 h.
The mixture is subsequently partitioned between ethyl acetate and water, and the organic phase is washed three times with water and dried over Na2SO4 and evaporated in a rotary evaporator.
The residue remaining is recrystallised from heptane/toluene.
The yield is 43 g (0.15 mol, 38percent).
38% With palladium diacetate; sodium hydrogencarbonate; tris-(o-tolyl)phosphine In 1,2-dimethoxyethane for 16 h; Reflux 75 g (0.41 mol) of 1,3,5-trichloro-pyrimidine, 100 g (0.82 mol) of phenylboronic acid and 625 ml of a 4M solution of NaHCO3 to 2.5 l of ethylene glycol dimethyl ether and the suspension was. 2.3 g (10.23 mmol) of Pd (OAc) 2 and 10.35 g (34 mmol) of P (o-Tol) 3 was added to the suspension, and the reaction mixture was refluxed underIt was heated for 16 hours.Then, the mixture was partitioned between ethyl acetate and water, the organic phase was washed with water three times, dried over Na2SO4, and evaporated in a rotary evaporator. The remaining residue was recrystallized from heptane / toluene.The yield was 43 g (0.15 mol, 38percent).
6.46 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water for 2 h; Reflux; Inert atmosphere Under nitrogen flow , the of 10 g of 2,4,6-trichloropyrimidine, 13.3g of Phenylboronic acid, 2M of Aqueous solution of sodium carbonate 163.5ml, 1,2-dimethoxyethane 545ml with Bis(triphenylphosphine)palladium(II)dichloride mixture solution was refluxedthe for 2h . After cooling to room temperature, extraction was carried out withtoluene. The organic layer was washed twice with water, dried with sulfuricacid and evaporated. The resulting concentrate was purified by columnchromatography on silica gel and dried in vacuo to obtain 6.46 g of 2-chloro-4,6-diphenylpyrimidine.

Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 21, p. 7125 - 7128
[2] Patent: WO2011/93609, 2011, A1, . Location in patent: Page/Page column 17
[3] Patent: KR2015/92145, 2015, A, . Location in patent: Paragraph 0265-0267
[4] Patent: CN103664906, 2016, B, . Location in patent: Paragraph 0158; 0160
[5] Patent: CN103570628, 2016, B, . Location in patent: Paragraph 0103-0106
[6] Patent: CN103664937, 2016, B, . Location in patent: Paragraph 0084-0089
[7] Patent: CN103664894, 2016, B, . Location in patent: Paragraph 0201; 0205; 0207
[8] Patent: CN103665014, 2017, B, . Location in patent: Paragraph 0131; 0135-0137
[9] Dyes and Pigments, 2018, vol. 157, p. 377 - 384
[10] Patent: EP2489664, 2012, A1, . Location in patent: Page/Page column 43-44
[11] Patent: WO2011/71255, 2011, A1, . Location in patent: Page/Page column 14; 15
[12] Patent: KR2016/5944, 2016, A, . Location in patent: Paragraph 0242-0245
[13] Patent: EP2415769, 2012, A1, . Location in patent: Page/Page column 114-115
[14] Patent: US9711732, 2017, B2, . Location in patent: Page/Page column 225
[15] Patent: US9966541, 2018, B2, . Location in patent: Page/Page column 99
[16] Patent: WO2011/136520, 2011, A1, . Location in patent: Page/Page column 13
[17] Patent: WO2011/10839, 2011, A1, . Location in patent: Page/Page column 17-18
[18] Patent: WO2011/99718, 2011, A1, . Location in patent: Page/Page column 13-14
[19] Patent: WO2013/12298, 2013, A1, . Location in patent: Paragraph 111-112
[20] Patent: WO2006/55725, 2006, A2, . Location in patent: Page/Page column 175
[21] Patent: WO2004/99159, 2004, A1, . Location in patent: Page 35-36; 53; 90
[22] Patent: WO2004/99171, 2004, A2, . Location in patent: Page 112
[23] Patent: US2013/53558, 2013, A1, . Location in patent: Paragraph 0167; 0168
[24] Patent: KR2015/93836, 2015, A, . Location in patent: Paragraph 0211-0213
[25] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 1, p. 127 - 131
[26] Patent: TWI523840, 2016, B, . Location in patent: Page/Page column 54
  • 2
  • [ 3764-01-0 ]
  • [ 24388-23-6 ]
  • [ 2915-16-4 ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃; Phenylboronic acid pinacol ester (22.3 g, 109 mmol), THF (240 ml), 2, 4, 6-trichloropyrimidine (10 g, 54.5 mmol), Pd (PPh 3) 4 (3.8 g, 3.27 mmol), K 2 CO 3 (45.2 g, 327 mmol), water (120 ml) adding an 90 °C stirring section. When reaction is completed CH 2 Cl 2 and a water extraction of organic layer after MgSO 4 to dry a formed after silicagel column are 9.5 g obtained for the products and recrystallization. (Yield: 65percent)
Reference: [1] Patent: KR2016/41391, 2016, A, . Location in patent: Paragraph 0210; 0212; 0213
  • 3
  • [ 4120-05-2 ]
  • [ 2915-16-4 ]
YieldReaction ConditionsOperation in experiment
95.4% for 6 h; Heating / reflux 86.9 g (0.35 mol) of 2-hydroxy-4,6-diphenyl-1,3-pyrimidine (compound 2) are stirred in 400 ml (4.38 mol) of phosphoryl chloride under reflux for 6 hours. The reaction mixture is cooled to 20-25° C. and added dropwise to 4 l of water. The beige precipitate is filtered off, washed with water and dried in a vacuum oven. 89.0 g (=95.4percent yield) of beige crystals are obtained of the formula [C00058] [00401] with a melting point of 112-114° C. [00402] Examples A4 to A10 and A12 to A13 illustrate the preparation of the compounds according to the invention
Reference: [1] Patent: US6706215, 2004, B1, . Location in patent: Page column 40-41
[2] Synthetic Communications, 1991, vol. 21, # 7, p. 901 - 906
  • 4
  • [ 98-80-6 ]
  • [ 2915-16-4 ]
YieldReaction ConditionsOperation in experiment
0.15 mol, 38% With sodium hydrogencarbonate In 1,2-dimethoxyethane a)
2-Chloro-4,6-diphenylpyrimidine
75 g (0.41 mmol) of 1,3,5-trichloropyrimidine, 100 g (0.82 mol) of phenylboronic acid and 625 ml of 4 M NaHCO3 solution are suspended in 2.5 l of ethylene glycol dimethyl ether. 2.3 g (10.23 mmol) of Pd(OAc)2 and 10.35 g (34 mmol) of (o-Tol)3P are added to this suspension, and the reaction mixture is heated under reflux for 16 h.
The mixture is subsequently partitioned between ethyl acetate and water, and the organic phase is washed three times with water and dried over Na2 SO4 and evaporated in a rotary evaporator.
The residue which remains is recrystallised from heptane/toluene.
The yield is 43 g (0.15 mol, 38percent).
Reference: [1] Patent: US2012/97899, 2012, A1,
  • 5
  • [ 4120-05-2 ]
  • [ 2915-16-4 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 29, p. 7167 - 7179
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 153 - 158
  • 6
  • [ 120-46-7 ]
  • [ 2915-16-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 153 - 158
[2] Synthetic Communications, 1991, vol. 21, # 7, p. 901 - 906
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Similarity: 0.81

Chemical Structure| 13036-50-5

[ 13036-50-5 ]

2-Chloro-4-phenylpyrimidine

Similarity: 0.79

Chlorides

Chemical Structure| 29874-83-7

[ 29874-83-7 ]

2-Chloro-4-phenylquinazoline

Similarity: 0.96

Chemical Structure| 32785-40-3

[ 32785-40-3 ]

2-Chloro-4-methyl-6-phenylpyrimidine

Similarity: 0.88

Chemical Structure| 6141-14-6

[ 6141-14-6 ]

2-Chloro-4-methylquinazoline

Similarity: 0.84

Chemical Structure| 54994-35-3

[ 54994-35-3 ]

2-Chloro-6-phenylpyrimidin-4-amine

Similarity: 0.83

Chemical Structure| 945016-63-7

[ 945016-63-7 ]

3-(2-Chloropyrimidin-4-yl)-1H-indole

Similarity: 0.81

Related Parent Nucleus of
[ 2915-16-4 ]

Pyrimidines

Chemical Structure| 32785-40-3

[ 32785-40-3 ]

2-Chloro-4-methyl-6-phenylpyrimidine

Similarity: 0.88

Chemical Structure| 54994-35-3

[ 54994-35-3 ]

2-Chloro-6-phenylpyrimidin-4-amine

Similarity: 0.83

Chemical Structure| 945016-63-7

[ 945016-63-7 ]

3-(2-Chloropyrimidin-4-yl)-1H-indole

Similarity: 0.81

Chemical Structure| 40230-24-8

[ 40230-24-8 ]

4,6-Diphenylpyrimidin-2-amine

Similarity: 0.81

Chemical Structure| 13036-50-5

[ 13036-50-5 ]

2-Chloro-4-phenylpyrimidine

Similarity: 0.79