10325-70-9

Basic information

• Product Name: 1-(5-Pyrimidinyl)ethanone
• Synonyms: Ethanone,1-(5-pyrimidinyl)-;Ethanone, 1-(5-pyrimidinyl)- (9CI);1-(5-Pyrimidinyl)ethanone;5-Acetylpyrimidine;1-(pyrimidin-5-yl)ethanone;1-(Pyrimidin-5-yl)ethan-1-one;1-(Pyrimidin-5-yl)ethan-1-one, 5-Ethanoylpyrimidine;5-EthanoylpyriMidine
• CAS NO: 10325-70-9
• Molecular Formula: C₆H₆N₂O
• Molecular Weight: 122.12
• Product Categories: ACETYLGROUP;PYRIMIDINE;Amines;Aromatics;Heterocycles;Heterocycle-Pyrimidine series
• Mol File: 10325-70-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 87-88 °C
• Boiling Point: 224.5 °C at 760 mmHg
• Flash Point: 92.1℃
• Appearance: white powder
• Density: 1.136
• Vapor Pressure: 0.0909mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.03±0.10(Predicted)
• CAS DataBase Reference: 1-(5-Pyrimidinyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-Pyrimidinyl)ethanone(10325-70-9)
• EPA Substance Registry System: 1-(5-Pyrimidinyl)ethanone(10325-70-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 10325-70-9(Hazardous Substances Data)

Usage

Uses

5-Acetylpyrimidine is a substituted pyrimidine used in the study for prediction of relative potency of ketone protease inhibitors using molecular orbital theory.

InChI:InChI=1/C6H6N2O/c1-5(9)6-2-7-4-8-3-6/h2-4H,1H3

Synthetic route

5-(α-hydroxyethyl)pyrimidine (79691-74-0) → 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9)

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 3h;	73%
With dipyridinium dichromate; 4 A molecular sieve; acetic acid In dichloromethane at 20℃; for 0.333333h;	67%

5-bromopyrimidine (4595-59-9) + N-Methoxy-N-methylacetamide (78191-00-1) → 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9)

Conditions	Yield
Stage #1: 5-bromopyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78 - 0℃;	45%
Stage #1: 5-bromopyrimidine With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran at -78℃; for 1h;	175 mg

1-(4,6-dichloropyrimidine-5-yl)ethane-1-one (60025-06-1) → 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9)

Conditions	Yield
With hydrogen; magnesium oxide; palladium on activated charcoal In ethanol for 8h;	34%

2-methylimidazole (693-98-1) + C6H5N2O(1-)*K(1+) → potassium 2-methylimidazolate + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9)

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

9-Phenylfluorene (789-24-2) + C6H5N2O(1-)*K(1+) → potassium 9-phenylfluorenide (27839-58-3) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9)

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

pyrimidine-5-carbaldehyde (10070-92-5) → 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / diethyl ether / 1 h / 20 °C 2: 67 percent / molecular sieves 4 Angstroem; pyridinium dichromate; HOAc / CH2Cl2 / 0.33 h / 20 °C View Scheme

4,6-dichloro-5-(α-hydroxyethyl)pyrimidine (60025-05-0) → 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / H2, MgO / 10percent Pd/C / ethanol / 12 h / Heating 2: 73 percent / MnO2 / CH2Cl2 / 3 h View Scheme

(2-amino-3-bromophenyl)methanol (397323-70-5) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 8-bromo-2-(pyrimidin-5-yl)quinoline

Conditions	Yield
Stage #1: (2-amino-3-bromophenyl)methanol With manganese(IV) oxide In ethanol at 80℃; for 1h; Sealed tube; Inert atmosphere; Stage #2: 1-(pyrimidin-5-yl)ethan-1-one With potassium hydroxide In ethanol at 0℃; for 1h; Friedlaender Quinoline Synthesis; Inert atmosphere; Sealed tube;	88%

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 3-methyl-isoxazolo[5,4-d]pyrimidine + (E)-1-(pyrimidin-5-yl)-ethanone oxime (349493-40-9)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydrogencarbonate In benzene for 2h; Heating;	A n/a B 78%

o-fluorobromobenzene (1072-85-1) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → C12H9FN2O (1213251-48-9)

Conditions	Yield
With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran; 1,4-dioxane; toluene at 100℃; for 18h;	76%

4-bromo-benzaldehyde (1122-91-4) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → C13H9BrN2O

Conditions	Yield
With sodium carbonate In methanol; water at 20℃; for 1h;	69%

N-methoxylamine hydrochloride (593-56-6) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → (Z)-1-(pyrimidin-5-yl)-ethanone O-methyloxime + (E)-1-(pyrimidin-5-yl)-ethanone O-methyloxime (349493-42-1)

Conditions	Yield
Stage #1: N-methoxylamine hydrochloride With sodium hydrogencarbonate In methanol at 20℃; for 0.5h; Stage #2: 1-(pyrimidin-5-yl)ethan-1-one In methanol at 20℃; for 1h;	A n/a B 63%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → (E)-3-(dimethylamino)-1-(pyrimidin-5-yl)prop-2-en-1-one (1232062-67-7)

Conditions	Yield
In isopropyl alcohol at 100℃; for 24h;	59%
for 2h; Reflux;	657 mg

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 2-bromo-1-(pyrimidin-5-yl)ethan-1-one (58004-79-8)

Conditions	Yield
With hydrogen bromide; bromine; acetic acid for 24h;	50%
With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; triethylamine In tetrahydrofuran at 0℃; for 0.5h;

(R,E)-N-(1-(2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide (1585971-57-8) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide (1616100-96-9)

Conditions	Yield
Stage #1: 1-(pyrimidin-5-yl)ethan-1-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: (R,E)-N-(1-(2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide In N,N-dimethyl-formamide; mineral oil at -10 - -5℃; for 1.5h; Inert atmosphere;	46.4%
Stage #1: 1-(pyrimidin-5-yl)ethan-1-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: (R,E)-N-(1-(2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide In tetrahydrofuran; hexane at -78 - -30℃; for 5h; Inert atmosphere; stereoselective reaction;	44%

4-bromo-benzaldehyde (1122-91-4) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → C19H12BrN5

Conditions	Yield
With ammonium hydroxide; sodium hydroxide In ethanol at 20℃; for 6h;	42.8%

6-bromoquinoxaline (50998-17-9) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → C14H10N4O (1213251-59-2)

Conditions	Yield
With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran; 1,4-dioxane; toluene at 100℃; for 18h;	42%

potassium 9-phenylfluorenide (27839-58-3) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 9-Phenylfluorene (789-24-2) + C6H5N2O(1-)*K(1+)

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

potassium 2-methylimidazolate + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 2-methylimidazole (693-98-1) + C6H5N2O(1-)*K(1+)

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 1-(3-methyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-ethanone O-methyl-oxime

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaHCO3 / methanol / 0.5 h / 20 °C 1.2: 63 percent / methanol / 1 h / 20 °C 2.1: acetone / Heating 3.1: NaBH4 / methanol / -30 - 20 °C View Scheme

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 5-{1-[(E)-Methoxyimino]-ethyl}-1-methyl-pyrimidin-1-ium; iodide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaHCO3 / methanol / 0.5 h / 20 °C 1.2: 63 percent / methanol / 1 h / 20 °C 2.1: acetone / Heating View Scheme

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 1-(5-pyrimidyl)-3-(dimethylamino)-2-propene-1-one (641615-34-1)

Conditions	Yield
for 15h; Heating / reflux;
for 15h; Heating / reflux;

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → N1-([4,5'-bipyrimidin]-2-yl)-6-methylbenzene-1,3-diamine (641615-36-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: isopropyl alcohol / 24 h / 100 °C 2.1: sodium hydroxide / isopropyl alcohol / 20 °C 3.1: hydrogenchloride; water / water / 2 h 3.2: pH > 8 View Scheme

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → N-(2-methyl-5-nitrophenyl)-4-(5-pyrimidinyl)-2-pyrimidineamine (641615-35-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: isopropyl alcohol / 24 h / 100 °C 2: sodium hydroxide / isopropyl alcohol / 20 °C View Scheme

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → N-[3-(4,5'-bipyrimdine-2-ylamino)-4-methylphenyl]-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indene-5-carboxamide (1232061-97-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: isopropyl alcohol / 24 h / 100 °C 2.1: sodium hydroxide / isopropyl alcohol / 20 °C 3.1: hydrogenchloride; water / water / 2 h 3.2: pH > 8 4.1: trimethylaluminum / toluene / 50 - 60 °C View Scheme

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 2-(2-propylpyridin-4-yl)-4-(pyrimidin-5-yl)thiazole

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; hydrogen bromide; bromine / 24 h 2: ethanol / 80 °C View Scheme

N-(6-bromo-5-chloropyridin-2-yl)-4-(tert-butyl)benzenesulfonamide + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → C21H21ClN4O3S

Conditions	Yield
With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 15h; Inert atmosphere;

N-(6-bromo-5-chloropyridin-2-yl)-4-(tert-butyl)benzenesulfonamide + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 4-(tert-butyl)-N-(5-chloro-6-(2-(hydroxyimino)-2-(pyrimidin-5-yl)ethyl)pyridin-2-yl)benzenesulfonamide

Conditions	Yield
Stage #1: N-(6-bromo-5-chloropyridin-2-yl)-4-(tert-butyl)benzenesulfonamide; 1-(pyrimidin-5-yl)ethan-1-one With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 15h; Inert atmosphere; Stage #2: With hydroxylamine hydrochloride; sodium hydroxide In methanol; water at 95℃; for 12h;	0.35 g

1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → 5-(1H-pyrazol-3-yl)pyrimidine

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / Reflux 2: hydrazine hydrate / ethanol / 1 h / 20 °C View Scheme

Upstream product

• 4595-59-9 5-bromopyrimidine 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 60025-05-0 4,6-dichloro-5-(α-hydroxyethyl)pyrimidine 
• 10070-92-5 pyrimidine-5-carbaldehyde 
• 789-24-2 9-Phenylfluorene 
• 693-98-1 2-methylimidazole 
• 79691-74-0 5-(α-hydroxyethyl)pyrimidine 
• 60025-06-1 1-(4,6-dichloropyrimidine-5-yl)ethane-1-one 

Downstream Products

• 641615-36-3 N₁-([4,5'-bipyrimidin]-2-yl)-6-methylbenzene-1,3-diamine 
• 641615-35-2 N-(2-methyl-5-nitrophenyl)-4-(5-pyrimidinyl)-2-pyrimidineamine 
• 1232061-97-0 N-[3-(4,5'-bipyrimdine-2-ylamino)-4-methylphenyl]-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indene-5-carboxamide 
• 641615-34-1 1-(5-pyrimidyl)-3-(dimethylamino)-2-propene-1-one 
• 349493-40-9 (E)-1-(pyrimidin-5-yl)-ethanone oxime 
• 1213251-48-9 C₁₂H₉FN₂O 
• 693-98-1 2-methylimidazole 
• 789-24-2 9-Phenylfluorene 
• 58004-79-8 2-bromo-1-(2-pyrimidin-5-yl)ethanone 
• 1616100-96-9 (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide 

Relevant articles and documents

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It is shown that the use of benzene as the solvent in the preparation of 2- and 4-acetylpyrimidines from cyanopyrimidines via the Grignard reaction makes this reaction a practical method for the preparation of pyrimidinyl ketones.Preparatively convenient methods for the preparation of 4-acetylpyrimidine from 4-ethylpyrimidine through the α-oximino derivative and 5-acetylpyrimidine from 4,6-dichloro derivatives of pyrimidine are proposed.