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CAS No.: | 830346-48-0 |
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Name: | 5-Bromo-1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-1H-pyrimidine-2,4-dione |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C13H9BrF4N2O2 |
Molecular Weight: | 381.124 |
Synonyms: | 5-bromo-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione;5-bromo-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methylpyrimidine-2,4-dione; |
Density: | 1.684±0.06 g/cm3(Predicted) |
Melting Point: | >230°C (dec.) |
PSA: | 55.12000 |
LogP: | 3.22600 |
1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
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With bromine In acetic acid at 20℃; | 97.5% |
With bromine; acetic acid for 14h; | 96% |
With bromine; acetic acid at 20℃; for 3h; | 87% |
5-bromo-6-methyluracil
1-(bromomethyl)-2-fluoro-6-(trifluoromethyl)benzene
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 75 - 85℃; | 81% |
N-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}urea
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
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Multi-step reaction with 2 steps 1: sodium iodide / acetonitrile / 20 h / 0 - 20 °C 2: bromine; acetic acid / 2 h View Scheme | |
Multi-step reaction with 2 steps 1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 16 h / 0 - 25 °C / Inert atmosphere 2: acetic acid; bromine / 14 h View Scheme |
2-fluoro-6-(trifluoromethyl)benzonitrile
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: borane-THF / tetrahydrofuran / 60 °C / Heating / reflux 1.2: 20 °C 2.1: hydrogenchloride; water / 6 h / Heating / reflux 3.1: sodium iodide / acetonitrile / 20 h / 0 - 20 °C 4.1: bromine; acetic acid / 2 h View Scheme |
(2-fluoro-6-(trifluoromethyl) phenyl)methanamine
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride; water / 6 h / Heating / reflux 2: sodium iodide / acetonitrile / 20 h / 0 - 20 °C 3: bromine; acetic acid / 2 h View Scheme | |
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 12 h / 100 °C 2: sodium iodide; chloro-trimethyl-silane / acetonitrile / 16 h / 0 - 25 °C / Inert atmosphere 3: acetic acid; bromine / 14 h View Scheme |
N-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}urea
ethyl 2-bromoacetoacetate
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
---|---|
With trimethylsilyl bromide In N,N-dimethyl acetamide at 0 - 80℃; for 16h; Inert atmosphere; | 32.7 g |
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
(R)-N-(tert-butoxycarbonyl)phenylglycinol
{(R)-2-[5-bromo-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; | 100% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 14h; | 99% |
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In toluene at 5 - 20℃; | 70% |
N-(benzyloxycarbonyl)-1(R)-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-3-[N-(benzyloxycarbonyl)-1(R)-1,2,3,4-tetrahydroisoquinoline]methylpyrimidine-2,4(1H,3H)-dione
Conditions | Yield |
---|---|
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; | 100% |
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
5-(2-fluoro-3-methoxyphenyl)-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methylpyrimidine-2,4(1H,3H)-dione
Conditions | Yield |
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With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In dimethyl sulfoxide at 60 - 70℃; for 6h; Inert atmosphere; | 83% |
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
(2-fluoro-3-methoxyphenyl)boronic acid
5-(2-fluoro-3-methoxyphenyl)-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methylpyrimidine-2,4(1H,3H)-dione
Conditions | Yield |
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Stage #1: (2-fluoro-3-methoxyphenyl)boronic acid With potassium iodide; potassium hydroxide In water; acetone at 25 - 30℃; for 0.166667h; Inert atmosphere; Stage #2: 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione With tri tert-butylphosphoniumtetrafluoroborate In water; acetone at 25 - 45℃; for 0.583333h; Inert atmosphere; Further stages; | 79.2% |
Stage #1: 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione; (2-fluoro-3-methoxyphenyl)boronic acid With potassium hydroxide In water; acetone for 0.5h; Stage #2: With palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate In water; acetone at 70℃; for 10h; | 76% |
Stage #1: 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione; (2-fluoro-3-methoxyphenyl)boronic acid With potassium hydroxide In water; acetone at 30℃; for 0.166667h; Stage #2: With palladium diacetate; ruphos In water; acetone at 30 - 52℃; for 6h; |