10320-42-0

Basic information

• Product Name: 2-Chloro-5-nitropyrimidine
• Synonyms: PYRIDINE, 2-CHLORO-5-NITRO-;PYRIMIDINE, 2-CHLORO-5-NITRO-;2-CHLORO-5-NITROPYRIMIDINE;CHLORO(2-)-5-NITROPYRIDINE;2-Chloro-5-nitropyrimidine 98%;2-Chloro-5-nitropyrimidine ,98%;2-Chloro-5-nitro-1,3-diazine
• CAS NO: 10320-42-0
• Molecular Formula: C₄H₂ClN₃O₂
• Molecular Weight: 159.53
• EINECS: 224-908-3
• Product Categories: FINE Chemical & INTERMEDIATES;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Pyrimidine series;Pyrazines, Pyrimidines & Pyridazines;Heterocycle-Pyrimidine series
• Mol File: 10320-42-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 105-108 °C(lit.)
• Boiling Point: 345.4 °C at 760 mmHg
• Flash Point: 162.7 °C
• Appearance: /
• Density: 1.6 g/cm³
• Vapor Pressure: 0.000124mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: ?20°C
• PKA: -4.60±0.22(Predicted)
• CAS DataBase Reference: 2-Chloro-5-nitropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-5-nitropyrimidine(10320-42-0)
• EPA Substance Registry System: 2-Chloro-5-nitropyrimidine(10320-42-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-41-37/38-22-20/21/22
• Safety Statements: 26-36-37/39-36/37/39-36/37-24/25
• RIDADR: UN 3335
• WGK Germany: 3
• RTECS: US7175000
• HazardClass: IRRITANT
• Hazardous Substances Data: 10320-42-0(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow solid

InChI:InChI=1/C4H2ClN3O2/c5-4-6-1-3(2-7-4)8(9)10/h1-2H

Synthetic route

2-hydroxy-5-nitropyrimidine (3264-10-6) → 2-Chloro-5-nitropyrimidine (10320-42-0)

Conditions	Yield
With trichlorophosphate for 0.5h; Heating;	97%
With N,N-dimethyl-aniline; trichlorophosphate for 2h; Heating / reflux;	54%

tert.-butylnitrite (540-80-7) + 5-nitropyrimidin-2-amine (3073-77-6) + copper(II) chloride (7447-39-4) → 2-Chloro-5-nitropyrimidine (10320-42-0)

Conditions	Yield
With magnesium sulfate In diethyl ether; acetonitrile	50%

5-nitropyrimidin-2-amine (3073-77-6) → 2-Chloro-5-nitropyrimidine (10320-42-0)

Conditions	Yield
With magnesium sulphate; tert.-butylnitrite; copper dichloride In acetonitrile at 65 - 80℃; for 0.5h;	50%

5-nitro-2(1H)-pyrimidinone (3264-10-6) → 2-Chloro-5-nitropyrimidine (10320-42-0)

Conditions	Yield
With trichlorophosphate

2-Chloro-5-nitropyrimidine (10320-42-0) + ethylene glycol (107-21-1) → 2-((5-nitropyrimidin-2-yl)oxy)ethanol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 80℃; for 0.333333h;	100%
With N-ethyl-N,N-diisopropylamine at 80℃; for 0.333333h;	100%

2-Chloro-5-nitropyrimidine (10320-42-0) → 2-((5-nitropyrimidin-2-yl)oxy)ethanol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethylene glycol at 80℃; for 0.333333h;	100%

2-Chloro-5-nitropyrimidine (10320-42-0) + sodium thiomethoxide (5188-07-8) → 2-(methylthio)-5-nitropyrimidine (14001-70-8)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	99%

Thiomorpholin (123-90-0) + 2-Chloro-5-nitropyrimidine (10320-42-0) → 4-(5-nitropyrimidin-2-yl)thiomorpholine (1562399-15-8)

Conditions	Yield
Stage #1: Thiomorpholin; 2-Chloro-5-nitropyrimidine In tetrahydrofuran; acetonitrile for 0.166667h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water; acetonitrile at 20℃; for 0.75h; Inert atmosphere;	99%

2-Chloro-5-nitropyrimidine (10320-42-0) → 2-chloro-5-aminopyrimidine (56621-90-0)

Conditions	Yield
With ethanol; iron; acetic acid for 6h; Reflux;	98%
With iron; acetic acid at 75℃; for 2h;	98%
With iron; acetic acid In ethanol; water at 70℃;	85%

2-Chloro-5-nitropyrimidine (10320-42-0) + N-(4-chloro-2,6-difluorophenyl)-7-(2-oxopyrrolidin-1-yl)-2,3-dihydro-1H-indole-5-sulfonamide → N-(4-chloro-2,6-difluorophenyl)-1-(5-nitropyrimidin-2-yl)-7-(2-oxopyrrolidin-1-yl)-2,3-dihydro-1H-indole-5-sulfonamide

Conditions	Yield
In tetrahydrofuran Reflux;	98%

2-Chloro-5-nitropyrimidine (10320-42-0) + aniline (62-53-3) → (5-nitro-pyrimidin-2-yl)-phenyl-amine (26806-61-1)

Conditions	Yield
In acetonitrile Inert atmosphere;	97%
With potassium carbonate In water; acetonitrile at 20℃; for 3h;
In acetonitrile at 20℃; for 4h; Inert atmosphere;

2-Chloro-5-nitropyrimidine (10320-42-0) + 1-amino-3-methylbenzene (108-44-1) → 5-nitro-N-(m-tolyl)pyrimidin-2-amine

Conditions	Yield
In acetonitrile Inert atmosphere;	97%
In acetonitrile at 20℃; for 4h; Inert atmosphere;

2-Chloro-5-nitropyrimidine (10320-42-0) + 2-Fluoroaniline (348-54-9) → N-(2-fluorophenyl)-5-nitropyrimidin-2-amine

Conditions	Yield
Inert atmosphere;	97%
In acetonitrile at 20℃; for 4h; Inert atmosphere;

2-Chloro-5-nitropyrimidine (10320-42-0) → 5-nitropyrimidin-2-amine (3073-77-6)

Conditions	Yield
With ammonium hydroxide In tetrahydrofuran at 20℃; for 1h;	96%

morpholine (110-91-8) + 2-Chloro-5-nitropyrimidine (10320-42-0) → 4-(5-nitropyrimidin-2-yl)morpholine (65735-66-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 72h;	95%
Stage #1: morpholine With triethylamine In tetrahydrofuran for 0.25h; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran at 27℃; for 12h;	86%
In acetonitrile at 20℃; for 3h;	61%
In tetrahydrofuran for 2h; Reflux;

2-Chloro-5-nitropyrimidine (10320-42-0) + 3-methyl-phenol (108-39-4) → 5-nitro-2-(m-tolyloxy)pyrimidine

Conditions	Yield
Stage #1: 3-methyl-phenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	95%

3,4-Dimethylphenol (95-65-8) + 2-Chloro-5-nitropyrimidine (10320-42-0) → 2-(3,4-dimethylphenoxy)-5-nitropyrimidine

Conditions	Yield
Stage #1: 3,4-Dimethylphenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	95%

2-Chloro-5-nitropyrimidine (10320-42-0) + 4-fluoroaniline (371-40-4) → N-(4-fluorophenyl)-5-nitropyrimidin-2-amine

Conditions	Yield
In acetonitrile Inert atmosphere;	95%
In acetonitrile at 20℃; for 4h; Inert atmosphere;

pyrrolidine (123-75-1) + 2-Chloro-5-nitropyrimidine (10320-42-0) → 5-nitro-2-(pyrrolidin-1-yl)pyrimidine (873090-71-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;	94%

2-Chloro-5-nitropyrimidine (10320-42-0) + piperazine-1-sulfonic acid dimethylamide (98961-97-8) → N,N-dimethyl-4-(5-nitropyrimidin-2-yl)piperazine-1-sulfonamide (1146543-74-9)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 24h;	92%
With triethylamine In tetrahydrofuran at 20℃; for 24h;	92%

2-Chloro-5-nitropyrimidine (10320-42-0) + N-(4-chloro-2,6-difluorophenyl)-7-(2-oxoimidazolidin-1-yl)-2,3-dihydro-1H-indole-5-sulfonamide → N-(4-chloro-2,6-difluorophenyl)-1-(5-nitropyrimidin-2-yl)-7-(2-oxoimidazolidin-1-yl)-2,3-dihydro-1H-indole-5-sulfonamide

Conditions	Yield
In tetrahydrofuran Reflux;	92%

1-methyl-piperazine (109-01-3) + 2-Chloro-5-nitropyrimidine (10320-42-0) → 2-(4-methylpiperazin-1-yl)-5-nitropyrimidine (943749-60-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	91%
Stage #1: 1-methyl-piperazine With triethylamine In tetrahydrofuran for 0.25h; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran at 27℃; for 12h;	83%

2-Chloro-5-nitropyrimidine (10320-42-0) + 4-bromo-phenol (106-41-2) → 2-(4-bromophenoxy)-5-nitropyrimidine

Conditions	Yield
Stage #1: 4-bromo-phenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%
With triethylamine In tetrahydrofuran at 20℃; for 3h;	294 mg

2-Chloro-5-nitropyrimidine (10320-42-0) + phenol (108-95-2) → 5-nitro-2-phenoxypyrimidine

Conditions	Yield
Stage #1: phenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	6.55 g
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	6.55 g

2-Chloro-5-nitropyrimidine (10320-42-0) + para-tert-butylphenol (98-54-4) → 2-(4-(tert-butyl)phenoxy)-5-nitropyrimidine

Conditions	Yield
Stage #1: para-tert-butylphenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%

2-Chloro-5-nitropyrimidine (10320-42-0) + 2,4-Xylenol (105-67-9) → 2-(2,4-dimethylphenoxy)-5-nitropyrimidine

Conditions	Yield
Stage #1: 2,4-Xylenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%

2-Chloro-5-nitropyrimidine (10320-42-0) + 4-methoxy-phenol (150-76-5) → 2-(4-methoxyphenoxy)-5-nitropyrimidine

Conditions	Yield
Stage #1: 4-methoxy-phenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%

2-Chloro-5-nitropyrimidine (10320-42-0) + 4-Fluorophenol (371-41-5) → 2-(4-fluorophenoxy)-5-nitropyrimidine

Conditions	Yield
Stage #1: 4-Fluorophenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%

2-Chloro-5-nitropyrimidine (10320-42-0) + 4-chloro-phenol (106-48-9) → 2-(4-chlorophenoxy)-5-nitropyrimidine

Conditions	Yield
Stage #1: 4-chloro-phenol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%

2-Chloro-5-nitropyrimidine (10320-42-0) + 4-Hydroxyacetophenone (99-93-4) → 1-(4-((5-nitropyrimidin-2-yl)oxy)phenyl)ethane-1-one

Conditions	Yield
Stage #1: 4-Hydroxyacetophenone With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%

2-Chloro-5-nitropyrimidine (10320-42-0) + o-hydroxyacetophenone (118-93-4) → 1-(2-((5-nitropyrimidin-2-yl)oxy)phenyl)ethane-1-one

Conditions	Yield
Stage #1: o-hydroxyacetophenone With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%

2-Chloro-5-nitropyrimidine (10320-42-0) + α-naphthol (90-15-3) → 2-(naphthalen-1-yloxy)-5-nitropyrimidine

Conditions	Yield
Stage #1: α-naphthol With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-Chloro-5-nitropyrimidine In tetrahydrofuran; mineral oil at 50℃; for 12h;	90%

2-Chloro-5-nitropyrimidine (10320-42-0) + o-toluidine (95-53-4) → 5-nitro-N-(o-tolyl)pyrimidin-2-amine

Conditions	Yield
In acetonitrile for 5h; Inert atmosphere;	90%
In acetonitrile at 20℃; for 4h; Inert atmosphere;

Upstream product

• 3073-77-6 5-nitropyrimidin-2-amine 
• 540-80-7 tert.-butylnitrite 
• 7447-39-4 copper(II) chloride 
• 3264-10-6 2-hydroxy-5-nitropyrimidine 
• 3264-10-6 5-nitro-2(1H)-pyrimidinone 

Downstream Products

• 1450-76-6 1-(2-hydroxy-5-nitrophenyl)ethanone 
• 88626-94-2 5-nitro-2-(diacetylmethyl)pyrimidine 
• 77696-49-2 5-nitro-2-(2,2-diphenylhydrazino)pyrimidine 
• 1275993-20-8 methyl 3-((1-(5-nitropyrimidin-2-yl)piperidin-4-yl)methoxy)benzoate 
• 1351341-78-0 [(3R,4S)-4-(2,5-difluorophenyl)-1-(5-nitropyrimidin-2-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester 

Relevant articles and documents

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BENZOTRIAZEPINONE DERIVATIVES

The present invention is concerned with benzotriazepinone derivatives, their intermediates, uses thereof and processes for their production. In particular, the present invention relates to parathyroid hormone (PTH) and parathyroid hormone related protein (PTHrp) receptor ligands, (PTH-1 or PTH/PTHrp receptor ligands). The invention also relates to methods of preparing such ligands and to compounds which are useful as intermediates in such methods.

THE SYNTHESIS AND SOME REACTIONS OF CHLOROPYRIMIDINES

Several chloro-hydroxy- and amino- chloropyrimidines have been prepared.The chloro groups have been replaced by hydrogen, mercapto, or hydroxyamino substituents to give useful synthetic intermediates.