13223-25-1

Basic information

• Product Name: 2-Chloro-4,6-dimethoxypyrimidine
• Synonyms: 2-CHLORO-4,6-DIMETHOXYPYRIMIDINE;4-methoxybenzoicacidsodium;PYRIMIDINE, 2-CHLORO-4,6-DIMETHOXY-;2-CHLOR-4,6-DIMETHOXYPYRIMIDINE;2-CHLORO-4,6-DIMETHOXYPYRIMIDINE 98+%;4,6-diMethoxypyriMidine-2-chloro;2-Chloro-4,6-dimethoxypyrimidine >=98.0%
• CAS NO: 13223-25-1
• Molecular Formula: C₆H₇ClN₂O₂
• Molecular Weight: 174.58
• EINECS: 1308068-626-2
• Product Categories: Pyrimidine;Pyrimidines;Building Blocks;Heterocyclic Building Blocks;Dimethoxy pyrimidines;NULL;Heterocycle-Pyrimidine series
• Mol File: 13223-25-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 100-105 °C
• Boiling Point: 317.1 °C at 760 mmHg
• Flash Point: 145.6 °C
• Appearance: white powder
• Density: 1.285 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.46±0.30(Predicted)
• BRN: 880035
• CAS DataBase Reference: 2-Chloro-4,6-dimethoxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4,6-dimethoxypyrimidine(13223-25-1)
• EPA Substance Registry System: 2-Chloro-4,6-dimethoxypyrimidine(13223-25-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 13223-25-1(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 13223-25-1 differently. You can refer to the following data:
1. 2-Chloro-4,6-dimethoxypyrimidine is used as building block in chemical synthesis. Product Data Sheet
2. 2-Chloro-4,6-dimethoxypyrimidine is a useful reactant for the synthesis of polycyclic fused and spiro-?4-?aminopyridines

Synthetic route

methyl 3-amino-3-methoxy-N-nitrile-2-propionamidine → 2-chloro-4,6-dimethoxypyrimidine (13223-25-1)

Conditions	Yield
With hydrogenchloride In methanol at 5℃; for 2h; Temperature;	82.1%

4,6-dimethoxy-2-aminopyrimidine (36315-01-2) → 2-chloro-4,6-dimethoxypyrimidine (13223-25-1)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium nitrite In water; ethyl acetate	29.9%
With hydrogenchloride; zinc(II) chloride; sodium nitrite Chlorination;

2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-chloro-4,6-dimethoxy-5-nitro-pyrimidine (478010-54-7)

Conditions	Yield
With trifluoromethylsulfonic anhydride; tetramethylammonium nitrate In dichloromethane at 20℃; for 38h;	98%
Stage #1: 2-chloro-4,6-dimethoxypyrimidine With trifluoromethylsulfonic anhydride; tetramethylammonium nitrate In dichloromethane at 0 - 20℃; for 50.75h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	97%
With nitric acid; trifluoroacetic anhydride In dichloromethane at 20℃;	97%

phenylpropyolic acid (637-44-5) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-2-(phenylethynyl)pyrimidine (329206-02-2)

Conditions	Yield
With bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 10h;	98%

4-phenyl-1-piperazine (92-54-6) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-2-(4-phenyl-piperazin-1-yl)-pyrimidine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 0.0833333h; Irradiation;	97%

benzofuran-2-boronic acid (98437-24-2) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-(benzofuran-2-yl)-4,6-dimethoxypyrimidine (1251914-08-5)

Conditions	Yield
With (η3-indenyl)Pd(XPhos)(OTf); potassium carbonate In tetrahydrofuran; methanol at 40℃; for 1h; Suzuki-Miyaura Coupling; Glovebox; Sealed tube; Cooling with ethanol-dry ice;	97%
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In tetrahydrofuran; water at 40℃; for 0.5h; Suzuki-Miyaura cross-coupling; Inert atmosphere;	96%
With C46H64ClPPd; potassium carbonate In tetrahydrofuran; methanol at 40℃; for 1h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;	95%
With [(η3-1-tBu-indenyl)Pd(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(Cl)]; potassium carbonate In tetrahydrofuran; methanol at 20℃; for 3h; Reagent/catalyst; Time; Suzuki-Miyaura Coupling; Inert atmosphere;

2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-2-aminopyrimidine (36315-01-2)

Conditions	Yield
With ammonia In tetrahydrofuran; water at 100 - 110℃; for 4h; Solvent; Autoclave; Large scale;	96.3%
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Reagent/catalyst; Inert atmosphere;	80%
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 96 h / Reflux 2: methanol; palladium(II) hydroxide / 48 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 96 h / Reflux 2: hydrogen; palladium(II) hydroxide / methanol / 48 h / 20 °C / 760.05 Torr View Scheme

N-boc-2-pyrroleboronic acid (135884-31-0) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → C15H19N3O4

Conditions	Yield
With O4P(3-)*3K(1+)*5H2O; tris(1-adamantyl)phosphine; C28H26N2O8Pd2S2 In tetrahydrofuran; butan-1-ol at 20℃; for 5h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	96%
With O4P(3-)*3K(1+)*5H2O; tris(1-adamantyl)phosphine; {2-[((acetyl-κO)amino)phenyl-κC](tri-1-adamantylphosphine)palladium}(p-toluenesulfonate) In tetrahydrofuran; butan-1-ol at 20℃; for 5h; Suzuki-Miyaura Coupling;	96%

2-chloro-4,6-dimethoxypyrimidine (13223-25-1) + sodium thiomethoxide (5188-07-8) → 4,6-dimethoxy-2-(methylsulfanyl)pyrimidine (90905-46-7)

Conditions	Yield
In methanol at 45 - 50℃; for 2h;	95.6%

1-methyl-piperazine (109-01-3) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidine (871365-06-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 2.5h; Inert atmosphere;	95%
In N,N-dimethyl-formamide at 90℃; for 2.5h; Inert atmosphere;	95%

4-dibenzofurylboronic acid (100124-06-9) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-(dibenzo[b,d]furan-4-yl)-4,6-dimethoxypyrimidine (1334531-07-5)

Conditions	Yield
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one; water; toluene at 90℃; Suzuki-Miyaura cross-coupling; Continuous flow reactor; Inert atmosphere;	94%

4-(2-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester (955397-70-3) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → C22H28N4O4

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 120℃; for 12h; Inert atmosphere;	94%

2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-chloro-5-hydroxy-4,6-dimethoxypyrimidine

Conditions	Yield
Stage #1: 2-chloro-4,6-dimethoxypyrimidine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; Stage #2: With tert.-butylhydroperoxide; n-butyllithium In tetrahydrofuran; decane; n-heptane; ethylbenzene at -78 - 0℃; for 4h; Stage #3: With hydrogenchloride In tetrahydrofuran; decane; n-heptane; ethylbenzene; water pH=7;	93.4%
Stage #1: 2-chloro-4,6-dimethoxypyrimidine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; Inert atmosphere; Stage #2: With tert.-butylhydroperoxide; n-butyllithium In tetrahydrofuran; decane; hexane; n-heptane; ethylbenzene at -78 - 0℃; Inert atmosphere;	93.4%

benzylamine (100-46-9) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → N-benzyl-2-amino-4,6-dimethoxypyrimidine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 0.666667h; Irradiation;	93%
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	90%
With potassium carbonate In 1,4-dioxane for 96h; Reflux;	87%
With potassium carbonate In 1,4-dioxane for 96h; Reflux;	87%

sodium isocyanate (917-61-3) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) + tert-butyl alcohol (75-65-0) → tert-butyl (4,6-dimethoxypyrimidin-2-yl)carbamate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; triethylamine at 110℃; for 16h; Inert atmosphere;	93%

morpholine (110-91-8) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-2-(morpholin-4-yl)pyrimidine (1568908-87-1)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 2.5h; Inert atmosphere;	93%
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	84%

2-chloro-4,6-dimethoxypyrimidine (13223-25-1) + 7-mercapto-3-methyl-3H-isobenzofuran-1-one (135217-37-7) → 7-[(4,6-dimethoxy-pyrimidin-2-yl)thio]-3-methyl-phthalide (135186-78-6)

Conditions	Yield
With potassium carbonate; triphenylphosphine In acetonitrile at 55℃; for 23h;	91.1%

1-ethenylcyclohexene (931-49-7) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-(cyclohexenylethynyl)-4,6-dimethoxypyrimidine (1418137-10-6)

Conditions	Yield
With bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(0); caesium carbonate In acetonitrile at 90℃; for 5h; Sonogashira Cross-Coupling; Inert atmosphere;	91%
With potassium phosphate; bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride In acetonitrile at 90℃; for 6h; Sonogashira Cross-Coupling;	75%

sodium cyanamide (19981-17-0, 20611-81-8, 123092-13-7, 17292-62-5) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-cyanamino-4,6-dimethoxypyrimidine

Conditions	Yield
With 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere;	91%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → methyl 4,6-dimethoxypyrimidine-2-carboxylate

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium acetate at 165℃; under 11250.9 Torr; for 2h; Product distribution; various reaction conditions;	90%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium acetate at 165℃; under 11250.9 Torr; for 2h;	90%

3-hydroxy-pyridine-2-carbaldehyde-diethylacetal (104217-48-3) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetal (136429-20-4) + 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetate

Conditions	Yield
In water	A n/a B 90%

(S)-3-methylmorpholine (350595-57-2) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → (3S)-4-(4,6-dimethoxypyrimidin-2-yl)-3-methylmorpholine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 22h; Sealed tube;	90%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 22h;	90%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 22h; Sealed tube;	90%

1-butyn-4-ol (927-74-2) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-(but-3-ynyloxy)-4,6-dimethoxypyrimidine

Conditions	Yield
Stage #1: 3-Butyn-1-ol; 2-chloro-4,6-dimethoxypyrimidine With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: In tetrahydrofuran at 20℃; for 17h; Inert atmosphere;	90%

4-fluoroaniline (371-40-4) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-[(4-fluorophenyl)amino]-4,6-dimethoxypyrimidine (1627898-12-7)

Conditions	Yield
With Pd(PAd3)(4-FC6H4)Br; triethylamine In water; toluene at 100℃; for 16h; Inert atmosphere; Glovebox;	90%

4-phenylpiperidine (771-99-3) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-2-(4-phenylpiperidine-1-yl)pyrimidine

Conditions	Yield
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	88%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → ethyl 4,6-dimethoxy-2-pyrimidinecarboxylate (128276-49-3)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium acetate at 160℃; under 11250.9 Torr; for 2.5h;	87%

2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 2-iodo-4,6-dimethoxypyrimidine (1269417-63-1)

Conditions	Yield
With hydrogen iodide at 0 - 20℃; for 4h;	87%

pyrrolidine (123-75-1) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine (1622148-58-6)

Conditions	Yield
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	87%
Stage #1: pyrrolidine With sodium hydride In tetrahydrofuran for 0.5h; Reflux; Stage #2: 2-chloro-4,6-dimethoxypyrimidine In tetrahydrofuran for 48h; Reflux;	71%

indole (120-72-9) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 1-(4,6-dimethoxypyrimidin-2-yl)-1H-indole

Conditions	Yield
With C45H39BrNiOP2; lithium tert-butoxide; phenylboronic acid In toluene at 110℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;	87%

diphenylamine (122-39-4) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-N,N-diphenylpyrimidin-2-amine (1501945-27-2)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; cis-[1,1'-bis(diphenylphosphino)ferrocene](2-methylphenyl)nickel(II) chloride; acetonitrile; lithium tert-butoxide at 130℃; for 16h; Inert atmosphere;	86%

ethylenediamine (107-15-3) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → N-(1-aminoethan-2-yl)-2-amino-4,6-dimethoxypyrimidine

Conditions	Yield
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	86%

(2-methyl-[1,1'-biphenyl]-3-yl)methanol (76350-90-8) + 2-chloro-4,6-dimethoxypyrimidine (13223-25-1) → 4,6-dimethoxy-2-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)pyrimidine

Conditions	Yield
Stage #1: (2-methyl[1,1'-biphenyl]-3-yl)methanol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: 2-chloro-4,6-dimethoxypyrimidine In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	83%

Upstream product

• 36315-01-2 4,6-dimethoxy-2-aminopyrimidine 
• 77087-96-8 methyl 3-amino-3-methoxy-N-nitrile-2-propionamidine 

Downstream Products

• 147353-26-2 2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde di-n-octylacetal 
• 110284-76-9 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)benzaldehyde 
• 113763-46-5 methyl 5-cyano-2-(4,6-dimethoxypyrimidin-2-yl)oxy benzoate 
• 57235-35-5 4,6-dimethoxy-2-mercapto-pyrimidine 
• 894400-16-9 2-(4-iodophenoxy)-4,6-dimethoxypyrimidine 
• 894400-90-9 N-(4-iodophenyl)-4,6-dimethoxypyrimidin-2-amine 
• 633320-99-7 (1S,2S)-2-(4,6-dimethoxypyrimidin-2-yl)cyclohexanecarboxylic acid 
• 83356-02-9 5-nitro-2,4,6-trimethoxypyrimidine 
• 127014-63-5 (+/-)-3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-dihydrofuranone 

Relevant articles and documents

Synthesis method of 2-chloro-4,6-dimethoxypyrimidine

The invention provides a synthesis method of 2-chloro-4,6-dimethoxypyrimidine and belongs to the technical field of organic synthesis. A synthesis route that malononitrile, methanol, acetyl chloride,hydrogen cyanamide and alkali liquor are taken as raw materials is adopted, malononitrile is dropwise added into a system of malononitrile and methanol, 1,3-dimethamidine dihydrochloride is directly obtained, then reaction is carried out with sodium bicarbonate and hydrogen cyanamide to obtain 3-amino-3-methoxy-N-nitrile-2-propyl amidine, and further reaction is carried out with hydrogen chloride,so that 2-chloro-4,6-dimethoxypyrimidine is obtained. The synthesis method provided by the invention has the advantages that tedious synthesis process and equipment of 1,3-dimethamidine dihydrochloride are eliminated, acetyl chloride is added into the malononitrile and methanol, and 1,3-dimethamidine dihydrochloride is directly obtained by virtue of a one-step method. The synthesis route of 1,3-dimethamidine dihydrochloride has the advantages that moisture is controlled to be extremely low, product quality is stable and yield is high.

Dimethoxypyrimidines as Novel Herbicides. Part 1. Synthesis and Herbicidal Activity of Dimethoxyphenoxypyrimidines and Analogues

A number of 6-(4-phenoxyphenoxy)pyrimidines and triazines were synthesized and their herbicidal activity was measured. Compounds with the methoxy groups at the 2- and 4-positions on the pyrimidine and triazine rings exhibited high herbicidal activity. Introduction of a substituent into the 5-position of the pyrimidine ring diminished the activity. In the phenoxyphenoxy substructure at the 6-position, the central ether bond can be replaced by a methylene group without loss of activity. The optimum substituent on the terminal phenyl ring was 3-trifluoromethyl. The compounds showed a strong Hill reaction inhibition, but unfortunately showed poor selectivity between weeds and crops. - Keywords: phenoxyphenoxypyrimidines; phenoxyphenoxy-s-triazines; Hill reaction inhibitors; 2,6-dimethoxy-4-pyrimidine; 2,6-dimethoxy-4--s-triazine; herbicides

2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoximes, preparation processes thereof, herbicides containing the same, and herbicidal compositions containing the same along with other active ingredient

Disclosed are herbicidally active pyrimidine derivatives of the formula STR1 wherein R represents a hydrogen atom or an etherifying group, e.g., a lower alkyl, lower alkenyl, lower alkynyl, phenyl-substituted lower alkenyl, lower haloalkenyl, cycloalkyl, substituted phenyl-substituted lower alkenyl or phenyl-substituted lower alkynyl group; or a group represented by the following formula: STR2 wherein R1 represents a hydrogen atom or a lower alkyl group, X a halogen atom or a lower alkyl or lower alkoxyl group, m and n individually 0-2, and when m is 2, both Xs may be the same or different, and herbicidal compositions containing the same, alone or in combination with another herbicidally active compound, the pyrimidine derivatives being prepared by reaction of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldehyde with NH2 OR or with a salt of hydroxylamine followed by reaction with a halide of the formula RY wherein R has the same value as above and Y is Cl, Br or I.