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CAS No. : | 3029-64-9 | MDL No. : | MFCD07636745 |
Formula : | C5Cl3N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IAJCAZVXGKGAQK-UHFFFAOYSA-N |
M.W : | 208.43 | Pubchem ID : | 250945 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.78 |
TPSA : | 49.57 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 : | No |
Log Kp (skin permeation) : | -5.58 cm/s |
Log Po/w (iLOGP) : | 1.57 |
Log Po/w (XLOGP3) : | 2.81 |
Log Po/w (WLOGP) : | 2.31 |
Log Po/w (MLOGP) : | 0.79 |
Log Po/w (SILICOS-IT) : | 2.87 |
Consensus Log Po/w : | 2.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.31 |
Solubility : | 0.103 mg/ml ; 0.000494 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.51 |
Solubility : | 0.0647 mg/ml ; 0.00031 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.59 |
Solubility : | 0.0532 mg/ml ; 0.000255 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.85 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
In 1,4-dioxane; | b 4-Chloro-2,6-bis-cyclopropylamino-pyrimidine-5-carbonitrile To a solution of 500 mg (2.4 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyano-pyrimidine</strong> in 30 ml of dioxane were added at room temperature 0.84 ml (4.8 mmol) of N-ethyl-diisopropylamine and 0.52 ml (7.2 mmol) of cyclopropylamine. The yellow reaction mixture was stirred at room temperature during 18 hours, then, for working-up, it was evaporated under reduced pressure. The residue obtained was then chromatographed on silica gel using a 3:1 mixture of dichloromethane and hexane as the eluent yielding 328 mg (1.3 mmol, 55percent of theory) of 4-chloro-2,6-bis-cyclopropylamino-pyrimidine-5-carbonitrile as a yellow solid; MS: [M+H]+=249. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; ethanol; dichloromethane; | a 4-Chloro-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile A solution of 10.0 g (48 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyano-pyrimidine</strong> in 150 ml of dioxane was treated at 0° C. with 16.4 ml (96 mmol) of N-ethyl-diisopropylamine, followed by 8.7 ml (144 mmol) of ethanolamine. While warming up to room temperature, yellowish solid material started to precipitate. The yellow solution was stirred overnight, then the resulting material was separated by filtration and the mother liquor evaporated to dryness. The residue was stirred with dichloromethane and the solid filtered. To eliminate the ethanolammonium chloride, the two combined solid fractions were treated with 100 ml of ethanol, thereupon the resulting product was washed with 150 ml of dichloromethane. After drying under reduced pressure, 10.45 g (40.6 mmol, 84.5 of theory) of 4-chloro-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile were obtained as a yellowish powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In thionyl chloride; | (iii) 2,4,6-Trichloro-5-cyano-pyrimidine A solution of 8.03 g (0.035 mol) of (E/Z)-2,4,6-trichloro-pyrimidine-5-carbaldehyde oxime in 85 ml of thionylchloride prepared at 0° C., was heated to room temperature, then, during 2 hours to reflux. For the working-up, the yellow reaction mixture was cooled to room temperature, then evaporated under reduced pressure to yield 7.57 g of crude 2,4,6-trichloro-5-cyano-pyrimidine as a yellow-brownish solid. For purification, the crude material was chromatographed on silica gel using a 5:1 mixture of cyclohexane and dichloromethane as the eluent giving 4.38 g (0.021 mol, 59percent of theory) of 2,4,6-trichloro-5-cyano-pyrimidine as a white solid; MS: [M]+=207. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | EXAMPLE T 5-Cyano-2,4,6-trichloro-pyrimidine Prepared [see C.A. 62, 7775 (1965)] from 5-carbamoyl-2,4,6-trihydroxy-pyrimidine, phosphorus oxychloride and dimethyl aniline (18 hours, 100°C). M.p. 123°C (petroleum ether b.p.: 100°-140°C); yield: 65percent of theory. 5-Cyano-4,6-dichloro-2-methylthio-pyrimidine was prepared in analogous manner from 5-carbamoyl-4,6-dihydroxy-2-methylthiopyrimidine and phosphorus oxychloride/diethyl aniline (4 hours, reflux). M.p. 107°C (petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.5% | 5-Cyano-4,6 -dichloro-2-thiomorpholino-pyrimidine (m.p. 99°C, yield: 4.5percent of theory) from 5-cyano-2,4,6 -trichloro-pyrimidine and thiomorpholine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | In methanol; | 5-Cyano-4,6 -dichloro-2-methoxy-pyrimidine (m.p. 156°C, yield: 10percent of theory) from 5-cyano-2,4,6-trichloro-pyrimidine and methanol (reaction time: 20 hours; reaction temperature: 65°C; without potassium carbonate). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether; water; | EXAMPLE VIII 4,6-Dichloro-2-diethylamino-5-pyrimidinecarbonitrile A stirred solution of 6.3 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 150 ml of diethyl ether was cooled to -10°, and a solution of 4.4 grams of diethylamine in 75 ml of diethyl ether was added dropwise. Upon complete addition, the reaction mixture was stirred at -10° for 1 hour. Water was added to the reaction mixture. The diethyl ether layer was separated and dried over magnesium sulfate. The mixture was filtered, and the filtrate was evaporated under reduced pressure to a residue. The residue was recrystallized from methylcyclohexane to give 3.8 grams of 4,6-dichloro-2-diethylamino-5-pyrimidinecarbonitrile; mp, 125°-126°. Analysis: Calculated for C9 H10 Cl2 N4: C,44.10; H,4.07; N,22.85; Found: C,44.l3; H,4.28; N,23.14. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether; | EXAMPLE XV 4-Chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile To a stirred solution of 6.3 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 150 ml of diethyl ether at 10° was added dropwise 8.8 grams of diethylamine in 150 ml of diethyl ether. Upon complete addition, the reaction mixture was allowed to warm to room temperature, where it was stirred for 16 hours. The reaction mixture was heated under reflux for 1 hour, then cooled to room temperature. The reaction mixture was washed with water, and the diethyl ether layer was separated. The aqueous layer was washed with diethyl ether. The ether layers were combined and dried over magnesium sulfate. The mixture was filtered, and the filtrate was evaporated under reduced pressure to a residue. The residue was recrystallized from petroleum ether to give crude 4-chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrachloromethane; diethyl ether; water; acetone; | EXAMPLE V 4,6-Dichloro-2-ethylamino-5-pyrimidinecarbonitrile A stirred solution of 12.9 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 150 ml of acetone was cooled to -10°, and 7.7 grams of an aqueous 70percent ethylamine solution was added dropwise during 2 hours. The temperature of the reaction mixture was maintained at -10° throughout the addition. Following complete addition, the reaction mixture was allowed to warm to room temperature, where it stood for 16 hours. Then most of the acetone was removed by evaporation under reduced pressure. The residue was extracted with a mixture of water and diethyl ether. The ether layer was separated and dried over magnesium sulfate. The dried ether layer was filtered, and the ether was removed under reduced pressure. The residue was recrystallized from a mixture of methylcyclohexane and benzene, then from carbon tetrachloride, to give 4.2 grams of 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile; mp, 145-150°. Analysis: Calculated for C7 H6 Cl2 H4: C,38.74; H,2.78; N,25.80; Found: C,38.47; H,2.97; N,25.90. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether; water; | EXAMPLE VI 4,6-Dichloro-2-isopropylamino-5-pyrimidinecarbonitrile A stirred solution of 4.2 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 100 ml of diethyl ether was cooled to between -5° and -10°, and a solution of 2.4 grams of isopropylamine in 100 ml of diethyl ether was added dropwise. Upon complete addition, water was added to the reaction mixture, and the ether layer was separated. The ethereal layer was dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure. The residue was recrystallized from methylcyclohexane to give 2.4 grams of 4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile; mp, 179°-181°. Analysis: Calculated for C8 H8 Cl2 N4: C,41.57; H,3.47; N,24.23; Found: C,41.33; H,3.35; N,23.97. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; acetone; | EXAMPLE IV 4,6-Dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile A stirred solution of 6.3 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 25 ml of acetone was cooled to -10°, and 2.5 grams of 2-amino-2-methylpropionitrile was added. With the reaction mixture at -10°, a solution of 1.3 grams of sodium hydroxide in 3.5 ml of water was added dropwise. Upon complete addition, the reaction mixture was stirred at -10° for 30 minutes. The acetone was removed under reduced pressure; the residue was extracted with diethyl ether, and the extract was separated and dried over magnesium sulfate. The extract was filtered, and the filtrate was evaporated under reduced pressure, yielding a residue. The residue was recrystallized from methylcyclohexane to give 3.1 grams of 4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile; mp, 154-158°. Analysis: Calculated for C9 H7 Cl2 N5: C,42.21; H,2.73; N,27.34; Found: C,42.26; H,2.92; N,27.35. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate; | EXAMPLE II 2,4,6-Trichloro-5-pyrimidinecarbonitrile A stirred mixture of 40 grams (24 ml) of phosphorus oxychloride and 9 grams of 2,4,6-trihydroxy-5-pyrimidinecarboxamide was refluxed for 1 hour. An additional 12 ml of phosphorus oxychloride was then added, and the mixture was refluxed for an additional 3 hours. The excess phosphorus oxychloride was removed by distillation, and the residue was poured into a mixture of ice and water. The aqueous mixture was extracted with chloroform. The extract was dried with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to a residue. The residue was sublimed to give 2 grams of 2,4,6-trichloro-5-pyrimidinecarbonitrile; mp, 117°-119°. The mass spectrum of the product was consistent with the assigned structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With ammonia; In 1,4-dioxane; at 20 - 80℃; | PREPARATION 982,4-Diamino-6-chloropyrimidine-5-carbonitrileA mixture of <strong>[3029-64-9]2,4,6-trichloropyrimidine-5-carbonitrile</strong> (200mg, 0.96 mmol) and a 0.5M solution of NH3 in dioxane (12ml, 6 mmol) and the mixture stirred at room temperature for 2h. The monosubstituted intermediate was obtained and 10 ml more of NH3 in dioxane were added and the mixture stirred at 80C over the weekend. A suspension was obtained, the solid filtered off and the filtrate concentrated to give a solid which was triturated in diethyl ether. The title compound was obtained as a beige solid (156mg, 78% yield).LRMS (m/z): 170 (M+1 )+. |
51% | With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 1h; | Step 3. 2,4-diamino-6- chloropyrimidin-5-formonitrile ; <strong>[3029-64-9]2,4,6-trichloropyrimidin-5-formonitrile</strong> (9 g, 43.5 mmol), dioxane (40 mL), and ammonium hydroxide (36%, 40 mL) were added to a 150-mL round-bottom flask, and heated to 50 C. to react for 1 hour. After the completion of the reaction, the resultant mixture was cooled to room temperature, followed by an addition of 50 mL of ice water, and then placed and cooled in an ice-bath and stirred for 1.5 hours. The resultant mixture was filtered to obtain a filter residue. The filter residue was washed with H2O to obtain a light yellow solid of 3.8 g. The yield was 51%. LCMS (ESI): m/z=170 (M+H)+. |
4.5 g | With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 3h; | Ammonium hydroxide (20 mL) was added to a solution of <strong>[3029-64-9]2,4,6-trichloropyrimidine-5-carbonitrile</strong> (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50 C. and stirred for 3 hrs. The reaction mixture was cooled to 10 C. and water (50 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford the compound depicted above as a white solid (4.5 g) 13H NMR (100 MHz, DMSO) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS m/z=169.9 (M+H)+. |
4.5 g | With ammonium hydroxide; In 1,4-dioxane; water; at 10 - 50℃; for 3h; | (2,4-diamino-6-chloropyrimidine-5-carbonitrile) Ammonium hydroxide (20 mL) was added to a solution of <strong>[3029-64-9]2,4,6-trichloropyrimidine-5-carbonitrile</strong> (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50 C. and stirred for 3 hrs. The reaction mixture was cooled to 10 C. and water (50 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to obtain the title compound as a white solid (4.5 g) 13H NMR (100 MHz, DMSO) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS m/z=169.9 (M+H)+. |
With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 3h; | 10624] Ammonium hydroxide (20 mE) was added to a solution of 2,4,6-trichioropyrimidine-5-carbonitrile (5.0 g, 24 mmol) in dioxane (20 mE) at room temperature. The solution was heated to 50 C. and stirred for 3 hrs. The reaction mixture was cooled to 10C. and added to water (50 mE). The resulting solid was filtered, washed with water, and dried under high vacuum to afford the title compound. 13R NMR(100 MHz, DM50) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS mlz=1 69.9 (M+H+). | |
With ammonium hydroxide; In 1,4-dioxane; at 10 - 50℃; for 3h; | Ammonium hydroxide (20 mL) was added to a solution of 2 ,4,6-tric&oropyrimidine- 5-carbonitrile (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50C and stirred for 3 hrs. The reaction mixture was cooled to 10C and water (50 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford the title compound as a white solid. 13C NMR (100 MHz, DMSO) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS m/z - 169.9 (M+H)+. | |
With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 3h; | Ammonium hydroxide (20 mL) was added to a solution of <strong>[3029-64-9]2,4,6-trichloropyrimidine-5-carbonitrile</strong> (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50 C. and stirred for 3 hours. The reaction mixture was cooled to 10 C. and water (50 mL) added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford 2,4-diamino-6-chloropyrimidine-5-carbonitrile. 13H NMR (100 MHz, DMSO) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS m/z=169.9 (M+H+). | |
With ammonium hydroxide; In 1,4-dioxane; at 20 - 50℃; for 3h; | Example 3, Preparation of a Compound of Formula (3) A. Preparation of a Compound of Formula (3) in which R4 is CN, R6 and R7 are N, and X is CI (2,4-diammo-6^chloiopyr^ Ammonium hydroxide (20 mL) was added to a solution of 2,4,6- trichloropyriniidine-5-carbonitrile (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50C and stirred for 3 hrs. The reaction mixture was cooled to 10C and water (50 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford the above compound. 13H NMR (100 MHz, DMSO) 64.8, 162.6, 161.9, 115.8, 77.6. ES MS mh = 169.9 (M+H) | |
0.8 g | With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 3h; | Ammonium hydroxide (4 mL) was added to a solution of 2,4,6-trichloropyrimidine-5- carbonitrile (1.0 g, 4.8 mmol) in dioxane (4 mL) at room temperature. The solution was warmed to 50C and stirred for 3 hrs. The reaction mixture was cooled to 10C and water (10 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford 2,4,6-triamino-pyrimidine-5 carbonitrile as a white solid (0.8 g). Mass Spectrum (ESI) m/e: 170 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium azide; In water; acetone; for 6h;Heating; | The mixture of trichloride 8 (4.17 g, 20 mmol) and sodium azide (5.2 g, 80 mmol) in 150 mL of aq. Acetone (5percent of water) was boiled for 6 h, then the solvent was removed under vacuum, and a solid residue was washed with water (200 mL), dried on air and recrystallized. Triazide 9 was obtained as a colorless solid (3.74 g, 82percent). mp 118-120 °C (EtOH). IR (microcrystals, max/cm?1): 2235m, 2213m, 2160vs, 2133s, 2096m, 1562s, 1530vs, 1421s, 1371vs, 1280w, 1239s, 1209vs, 1156m, 1136m, 1083w, 1030w, 1006m, 969w, 811m, 782vs, 742s, 696w. UV-vis,max /nm (log ): 249 (4.03), 275 (3.55), 295 (3.46), 304 (3.42). 13C-NMR: 80.9, 110.4, 162.7, 166.9. 15N-NMR: ?99.8, ?130.2, ?132.4, ?142.3, ?144.2, ?148.6, ?257.0, ?259.7. EIMS, 70 eV, m/z (rel.int.): 229 (4, M++1), 228 (30, M+), 92 (7, C3N4+), 90 (8, C4N3+), 78 (100, C3N3+), 68 (5, CN4+), 66 (31, C2N3+), 64 (70, C3N2+), 54 (11, CN3+), 52 (35, C2N2+), 50 (12, C3N+), 42 (12, N3+), 40 (18, CN2+), 38 (46, C2N+), 26 (9, CN+). Anal. Calcd. for C5N12 (228.13): C, 26.32; N, 73.68. Found: C, 26.55; N, 73.45percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.3% | 6.37 g (35 mmol) of phenoxazine was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent, and the mixture was stirred on a magnetic stirrer for 10 min under ice bath. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.Dissolve 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> in 40 mlThe N,N-dimethylformamide solution was added dropwise to the reaction system, and after the addition was completed, the reaction was carried out at room temperature for 24 hours. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 3.91 g of a white solid powder was obtained in a yield of 60.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.9% | 7.84 g (35 mmol) of 10,10-dimethyl-diphenyl phenyl siloxane was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent in an ice bath condition. Next, stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 3.94 g of a white solid powder was obtained in a yield of 50.9percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55.8% | 9.00 g (35 mmol) of 10-phenylphenol azine was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent under ice bath conditions.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 4.87 g of a white solid powder was obtained in a yield of 55.8percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.3% | 11.17 g (35 mmol) of 3,6-diphenyloxazole was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent under ice bath conditions.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.2.07 g (10 mmol) of 2,4,6-trichloro-5-cyanopyrimidine was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 5.31 g of a white solid powder was obtained in a yield of50.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.7% | 6.93 g (35 mmol) of thiazideAdd to a 250 ml three-necked flask and add 100 ml of N,N-dimethylformamide as the reaction solvent in an ice bath.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added in portions to the reaction flaskIn the middle, continue stirring for 1 h.Dissolve 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> in 40 ml of N,N-dimethylformylThe amine solution was added dropwise to the reaction system, and after the addition was completed, the reaction was carried out at room temperature for 24 hours. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 4.64 g of a white solid powder was obtained in a yield of 66.7percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In toluene; for 1h;Reflux; Inert atmosphere; | Under nitrogen protection, 6.28 g (25 mmol) of isopropyl carbazole,2.83 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong>, 1.92 g (20 mmol) of NaOBu-t, 1.92 g (0.2 mmol) (t-Bu)3HBF4, 0.09 g (0.1 mmol) Pd2 ( Dba) 3 was added to a 250 ml three-necked flask, 100 ml of toluene was added as a reaction solvent, the temperature was raised to reflux temperature, and the mixture was stirred overnight on a magnetic stirrer. After completion of the reaction, the reaction solution was dried to dryness, and the obtained crude product was purified from petroleum ether and methylene chloride (PE: DCM = 5:1) as a mobile phase. Intermediate 1 was obtained as a white solid powder weighing 4.70 g, yield 73.7percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.2% | 8.79 g (35 mmol) of isopropyl carbazole was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent, and the mixture was stirred on a magnetic stirrer for 10 min under ice-cooling. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. A white solid powder of 5.56 g was obtained in a yield of 65.2percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.2% | 8.79 g (35 mmol) of isopropyl carbazole was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent in an ice bath.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.4.97 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. Obtained 7.98 g of a white solid powder in a yield of50.2percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.1% | 7.32 g (35 mmol) of 9,9-dimethyl acridine was added to a 250 ml three-necked flask, 100 ml of N,N-dimethylformamide was added as a reaction solvent, and the mixture was stirred on a magnetic stirrer in an ice bath. 10min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 4.29 g of a white solid powder was obtained in a yield of 59.1percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In tetrahydrofuran; at -20 - 20℃; for 3h; | Solution of compound 1a (1mmol) was dissolved in 5ml of anhydrous tetrahydrofuran was added dropwise at -20C morpholine (4.5 mmol), dropwise warmed to room temperature for 3 hours, add 5ml of water to precipitate a white solid which was filtered, the filter cake was washed with ethanol weight crystallization or petroleum ether / ethyl acetate (5: 1) column chromatography to give compound 2a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Step 2. 2,4,6-trichloropyrimidin-5-formonitrile 2,4,6-trichloropyrimidin-5-carboxaldehyde (10 g, 47.4 mmol), hydroxylamine hydrochloride (3.3 g, 47.5 mmol), glacial acetic acid (100 mL), and H2O (5 mL) were added to a 150-mL round-bottom flask, and heated to 60 C. to react for 1 hour. After the completion of the reaction, the reaction solution was poured into crushed ice, and was extracted with CH2Cl2. The resultant organic phases were combined, washed with a saturated NaCl solution, dried with anhydrous Na2SO4, and then filtered and concentrated. The obtained substance was dissolved in SOCl2 (60 mL), reacted at room temperature for 10 minutes, and then heated for a reflux reaction for 2 hours. After the completion of the reaction, the resultant mixture was subjected to reduced pressure distillation to remove SOCl2 to give a residue, which was then dissolved in EtOAc and washed with H2O. The resultant organic phase was dried with anhydrous Na2SO4, filtered, and concentrated to obtain an oily substance of 9 g. The yield was 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at -40℃; for 2h;Inert atmosphere; | To a solution of 2, 4, 6-trichloropyrimidine-5-carbonitrile (25-a) (2.00 g, 9.60 mmol) in DMF (20 ml) at -40 under an atmosphere of nitrogen, was added trimethylamine (Et3N) (2.67 ml, 19.2 mmol) and (R) -cyclopropyl (2-methylpiperazin-1-yl) methanone (12-IA) (1.61 g, 9.60 mmol) . The resulting mixture was stirred for 2 h. After 2 h, the reaction was quenched via the addition of water (50 mL) and allowed to warm to ambient temperature. The mixture was extracted with EtOAc (3 x 100 mL) . The combined organic layers were washed with brine (100 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified via silica gel chromatography (50 g, 100-200 mesh) , eluting with 0-30%EtOAc in hexane to afford (R) -4, 6-dichloro-2- (4- (cyclopropanecarbonyl) -3-methylpiperazin-1-yl) pyrimidine-5-carbonitrile (25-c) . MS (ESI) Calc?d for (C14H16Cl2N5O) [M+H]+, 340; found, 340. |
Tags: 3029-64-9 synthesis path| 3029-64-9 SDS| 3029-64-9 COA| 3029-64-9 purity| 3029-64-9 application| 3029-64-9 NMR| 3029-64-9 COA| 3029-64-9 structure
[ 5305-45-3 ]
4,6-Dichloropyrimidine-5-carbonitrile
Similarity: 0.91
[ 1780-36-5 ]
2,4,6-Trichloro-5-methylpyrimidine
Similarity: 0.88
[ 3177-24-0 ]
2,4-Dichloropyrimidine-5-carbonitrile
Similarity: 0.87
[ 1277179-33-5 ]
2-Amino-4,6-dichloropyrimidine-5-carbonitrile
Similarity: 0.82
[ 50270-27-4 ]
2,4,6-Trichloropyrimidine-5-carbaldehyde
Similarity: 0.81
[ 5305-45-3 ]
4,6-Dichloropyrimidine-5-carbonitrile
Similarity: 0.91
[ 3177-24-0 ]
2,4-Dichloropyrimidine-5-carbonitrile
Similarity: 0.87
[ 1277179-33-5 ]
2-Amino-4,6-dichloropyrimidine-5-carbonitrile
Similarity: 0.82
[ 33097-13-1 ]
4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile
Similarity: 0.73
[ 1753-50-0 ]
2-Chloropyrimidine-5-carbonitrile
Similarity: 0.69
[ 5305-45-3 ]
4,6-Dichloropyrimidine-5-carbonitrile
Similarity: 0.91
[ 1780-36-5 ]
2,4,6-Trichloro-5-methylpyrimidine
Similarity: 0.88
[ 3177-24-0 ]
2,4-Dichloropyrimidine-5-carbonitrile
Similarity: 0.87
[ 1277179-33-5 ]
2-Amino-4,6-dichloropyrimidine-5-carbonitrile
Similarity: 0.82
[ 50270-27-4 ]
2,4,6-Trichloropyrimidine-5-carbaldehyde
Similarity: 0.81
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