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CAS No.: | 865758-96-9 |
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Name: | 2-[(6-Chloro-3,4-dihydro-3-Methyl-2,4-dioxo-1(2h)-pyriMidinyl)Methyl]benzonitrile |
Article Data: | 32 |
Molecular Structure: | |
Formula: | C13H10 Cl N3 O2 |
Molecular Weight: | 275.694 |
Synonyms: | 2-[(6-Chloro-3,4-dihydro-3-methyl-2,4-dioxo-1(2H; |
EINECS: | 695-742-0 |
Density: | 1.44 |
Melting Point: | 162-164°C |
Boiling Point: | 418.0±55.0 °C(Predicted) |
Solubility: | DMSO, Ehtyl Acetate, Methanol |
Appearance: | White to Off-White Solid |
PSA: | 67.79000 |
LogP: | 1.12038 |
3-methyl-6-chlorouracil
2-(bromomethyl)benzonitrile
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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Stage #1: 3-methyl-6-chlorouracil With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 23℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 2-(bromomethyl)benzonitrile In tetrahydrofuran at 65℃; for 2h; Schlenk technique; Inert atmosphere; | 96% |
With 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine at 60 - 65℃; for 3h; Large scale; | 96.42% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40 - 45℃; Solvent; Temperature; | 95.8% |
3-methyl-6-chlorouracil
2-cyanobenzyl chloride
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 60℃; for 1h; | 85.62% |
With potassium carbonate; potassium iodide In N,N-dimethyl acetamide at 50 - 100℃; |
2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile
dimethyl sulfate
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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Stage #1: 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.25h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide for 12h; Solvent; Reagent/catalyst; | 84.78% |
2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile
methyl iodide
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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Stage #1: 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile With sodium hydride; lithium bromide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 35℃; Further stages.; | 72% |
Stage #1: 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile With sodium hydride; lithium bromide In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; N,N-dimethyl-formamide at 20 - 35℃; Inert atmosphere; | 72% |
Stage #1: 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile With sodium hydride; lithium bromide In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 80℃; Inert atmosphere; | 70% |
methyl iodide
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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Stage #1: 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile With sodium hydride; lithium bromide In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 20 - 35℃; | 72% |
Stage #1: 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile With sodium hydride; lithium bromide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran; N,N-dimethyl-formamide at 20 - 35℃; | 72% |
1-(2-cyanobenzyl)-3-methylpyrimidine-2,4,6(1H,3H,5H)-trione
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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With phosphorus pentachloride; N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate In acetonitrile for 4 - 5h; Product distribution / selectivity; Reflux; | 70.5% |
1-(2-cyanobenzyl)-3-methylpyrimidine-2,4,6(1H,3H,5H)-trione
A
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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Stage #1: 1-(2-cyanobenzyl)-3-methylpyrimidine-2,4,6(1H,3H,5H)-trione With trichlorophosphate at 0℃; Stage #2: With water at 0 - 110℃; | A 37% B n/a |
2-(bromomethyl)benzonitrile
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide; dimethylsulfoxide / 0.5 h / 0 °C 1.2: LiBr / dimethylformamide; 1,2-dimethoxy-ethane / 0.25 h / 0 - 20 °C 1.3: 54 percent / dimethylformamide; dimethylsulfoxide / 0 - 20 °C 2.1: NaH; LiBr / dimethylformamide; tetrahydrofuran / 0.33 h / 20 °C 2.2: 72 percent / dimethylformamide; tetrahydrofuran / 0 - 35 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 0.25 h / 0 °C / Inert atmosphere 1.3: 0 - 20 °C / Inert atmosphere 2.1: sodium hydride; lithium bromide / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.33 h / 20 °C / Inert atmosphere 2.2: 20 - 35 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one; toluene / 70 - 80 °C 2: potassium carbonate / acetone / 50 - 60 °C View Scheme |
1-methyl-2,4,6-pyrimidinetrione
2-(bromomethyl)benzonitrile
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
Conditions | Yield |
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Stage #1: 1-methyl-2,4,6-pyrimidinetrione With N,N-dimethyl-aniline; trichlorophosphate In toluene at 90 - 95℃; for 2h; Stage #2: 2-(bromomethyl)benzonitrile With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60 - 65℃; Temperature; Concentration; | 40 g |
(R)-piperidin-3-ylcarbamic acid tert-butyl ester
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile
Conditions | Yield |
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With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 6h; Product distribution / selectivity; | 96% |
With potassium carbonate at 80 - 90℃; | 90% |
With tetrabutylammomium bromide; potassium carbonate; sodium iodide In acetonitrile for 25h; Reflux; | 89.3% |