5734-64-5

Usage

Uses

Used in Agricultural Industry:
2-Amino-4-chloro-6-methoxypyrimidine is used as a metabolite in the degradation process of chlorimuron-ethyl for [application reason] effective control of broad-leaved weeds in soybean and maize crops. Its presence in the degradation process contributes to the overall effectiveness of the herbicide in managing weed growth, thereby enhancing crop yield and quality.

InChI:InChI=1/C5H6ClN3O/c1-10-4-2-3(6)8-5(7)9-4/h2H,1H3,(H2,7,8,9)

Synthetic route

methanol (67-56-1) + 2-Amino-4,6-dichloropyrimidine (56-05-3) + sodium methylate (124-41-4) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
at 17℃; for 4.5h; Product distribution / selectivity; Heating / reflux;	97%
for 20h; Heating / reflux;	90%

2-Amino-4,6-dichloropyrimidine (56-05-3) + sodium methylate (124-41-4) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
In acetone at 17 - 30℃; for 6.5h; Product distribution / selectivity;	95.3%
In acetic acid methyl ester at 17 - 30℃; for 6.5h; Product distribution / selectivity;	94.6%
In methanol for 20h; Heating / reflux;	90%

methanol (67-56-1) + 2-Amino-4,6-dichloropyrimidine (56-05-3) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
With potassium carbonate at 20℃; for 2h; Product distribution / selectivity; Heating / reflux;	95%
With sodium methylate In methanol for 20h; Reflux;	90%
Stage #1: methanol With sodium hydride In tetrahydrofuran for 0.25h; Inert atmosphere; Stage #2: 2-Amino-4,6-dichloropyrimidine In tetrahydrofuran for 15h; Inert atmosphere;	84%

2,4-dichloro-6-methoxypyrimidine (43212-41-5) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
With ethanol; ammonia at 100℃;

2-amino-6-methoxy-3H-pyrimidin-4-one → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
With trichlorophosphate

2,4-dichloro-6-methoxypyrimidine (43212-41-5) + ammonia (7664-41-7) → 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5)

Conditions	Yield
at 100℃; im Rohr;

chlorimuron ethyl (90982-32-4) → 4-methoxypyrimidin-2-amine (155-90-8) + 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + ethyl 2-(aminosulfonyl)benzoate (59777-72-9) + saccharin (81-07-2) + N-(6-Chloro-4-methoxypyrimidin-2-yl)urea + chlorimuron + benzoic acid, ethyl benzoate

Conditions	Yield
With water for 2h; Product distribution; Rate constant; Irradiation; var. pH values;

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + N-methylaniline (100-61-8) → 2-amino-6-(N-methylanilino)pyrimidin-4(3H)-one (25706-78-9)

Conditions	Yield
at 289.84 - 299.84℃; for 0.0666667h;	97%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C14H9NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(phenoxycarbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C14H9NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	97%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) → 4-methoxypyrimidin-2-amine (155-90-8)

Conditions	Yield
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	94%
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	90%
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	90%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + <(4-nitrophenyl)oxy>sulfonyl isocyanate (73748-48-8) → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((4-nitrophenoxy) sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; <(4-nitrophenyl)oxy>sulfonyl isocyanate In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	94%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C10H9NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(ethoxycarbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C10H9NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	92%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 4-chlorobenzaldehyde (104-88-1) + diethyl malonate (105-53-3) → (S)-diethyl 2-(((4-chloro-6-methoxypyrimidin-2-yl)amino)(4-methoxyphenyl)methyl)malonate

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)((1S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In para-xylene at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	90%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C11H11NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(isopropoxycarbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C11H11NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	90%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C11H11NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(propoxycarbonyl) phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C11H11NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	89%

fur-2-ylboronic acid (13331-23-2) + 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) → 4-(furan-2-yl)-6-methoxypyrimidin-2-amine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 3h; Inert atmosphere;	87.29%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate (17823-58-4) → (E)-3-(4-Chloro-6-methoxy-pyrimidin-2-ylamino)-2-cyano-3-methylsulfanyl-acrylic acid ethyl ester

Conditions	Yield
With sodium hydride In N,N-dimethyl acetamide; toluene Ambient temperature;	85%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + Tetraethylene glycol (112-60-7) → 2-(2-(2-(2-(2-amino-6-methoxypyrimidin-4-yloxy)ethoxy)ethoxy)ethoxy)ethanol (1268273-35-3)

Conditions	Yield
Stage #1: Tetraethylene glycol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Reflux; Inert atmosphere; Stage #2: 2-amino-4-chloro-6-methoxypyrimidine In N,N-dimethyl-formamide at 80℃; for 3h;	83%
Stage #1: Tetraethylene glycol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2-amino-4-chloro-6-methoxypyrimidine In N,N-dimethyl-formamide; mineral oil at 80℃; for 3h; Inert atmosphere;	83%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 2-hydroxyphenyl 2-chloroethyl ether (4792-79-4) → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(2-chloroethoxy) phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; 2-hydroxyphenyl 2-chloroethyl ether In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	83%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C10H6F3NO6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-((2,2,2-trifluoroethoxy)carbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C10H6F3NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	83%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + N-butylamine (109-73-9) → N4-butyl-6-methoxypyrimidine-2,4-diamine

Conditions	Yield
With triethylamine In methanol at 70℃; for 12h;	82%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + benzyl alcohol (100-51-6) → 4-(benzyloxy)-6-methoxypyrimidin-2-amine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 3h; Solvent; Temperature; Inert atmosphere;	81.6%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 5-(4-Nitro-phenyl)-furan-2-carbonyl isothiocyanate (140160-21-0) → 1-(4-chloro-6-methoxy-pyrimidin-2-yl)-3-[5-(4-nitro-phenyl)-furan-2-carbonyl]-thiourea

Conditions	Yield
sonication;	81%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 5-(2-chlorophenyl)-2-furoylisothiocyanate (304437-60-3) → 1-(4-chloro-6-methoxy-pyrimidin-2-yl)-3-[5-(2-chloro-phenyl)-furan-2-carbonyl]-thiourea

Conditions	Yield
sonication;	81%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C9H7NO6S (73748-49-9) → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(methoxycarbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C9H7NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	81%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 4-Methoxybenzyl alcohol (105-13-5) → 4-methoxy-6-((4-methoxybenzyl)oxy)pyrimidin-2-amine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;	79.6%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 3-Isocyanatosulfonyl-1-methyl-1H-indole-2-carboxylic acid methyl ester → C17H16ClN5O6S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In benzene for 4h; Heating;	79%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 2-iodoethyl 2-hydroxybenzoate → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-((2-iodoethoxy)carbonyl)phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; 2-iodoethyl 2-hydroxybenzoate In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	79%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 2-tri-n-butylstannylpyridine (17997-47-6) → 4-methoxy-6-(pyridin-2-yl)pyrimidin-2-amine

Conditions	Yield
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 120℃; for 3h; Inert atmosphere;	78.91%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C9H8INO5S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(2-iodoethoxy) phenoxy)sulfonyl)amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C9H8INO5S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	78%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 2-fluoro-6-isocyanatosulfonyl-benzoic acid methyl ester → C14H12ClFN4O6S

Conditions	Yield
	75%

2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + C7H4N2O6S → sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-nitrophenoxy) sulfonyl) amide

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C7H4N2O6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	75%

formaldehyd (50-00-0) + 2-amino-4-chloro-6-methoxypyrimidine (5734-64-5) + 5-(4-fluorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione (41421-13-0) → 3-((4-chloro-6-methoxypyrimidin-2-ylamino)methyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole-2(3H)-thione

Conditions	Yield
In ethanol for 3h; Reflux;	74.5%

Upstream product

• 67-56-1 methanol 
• 56-05-3 2-Amino-4,6-dichloropyrimidine 
• 124-41-4 sodium methylate 
• 43212-41-5 2,4-dichloro-6-methoxypyrimidine 
• 7664-41-7 ammonia 
• 90982-32-4 chlorimuron ethyl 

Downstream Products

• 98525-48-5 2-amino-6-(diethylamino)-4-methoxypyrimidine 
• 155-90-8 4-methoxypyrimidin-2-amine 
• 1194-21-4 6-chloroisocytosine 
• 896448-88-7 C₁₅H₁₃Cl₃N₄O₃S 
• 1416567-35-5 C₁₅H₁₄BrClN₄O₆S 
• 1416567-37-7 C₁₅H₁₄ClIN₄O₆S 
• 1416567-42-4 C₂₁H₂₉ClN₄O₇SSi 
• 102909-18-2 C₁₅H₁₅ClN₄O₇S 
• 128569-20-0 C₁₄H₁₃ClN₄O₆S 
• 1416567-36-6 C₁₅H₁₄Cl₂N₄O₆S 
• 1620784-07-7 C₁₂H₉ClF₂N₄O₂ 

Relevant academic research and scientific papers

A novel benzoyl pyrimidine urea compound and its preparation and use (by machine translation)

The invention provides a benzoyl pyrimidine urea compound, of formula I or formula II structure shown. The present invention provides benzoyl pyrimidine urea compound has excellent armyworm killing, mosquito killing and broad-spectrum antifungal activity. The experimental result shows, the present invention provides benzoyl pyrimidine urea compound in 0.5 μg mL- 1 Sliding surface of larvae activity can be up to 100%, in the 0.25μg mL- 1 Sliding surface of larvae activity can be up to 100%. In the 50 μg mL- 1 When, demonstrated broad-spectrum antifungal activity, and to the cabbage in vitro blade has a certain protective effect. And low toxicity to fish, LC to the zebra fish50 Are respectively 378.387 mg L- 1 , 21.668 Mg L- 1 . Can be used to prepare insecticidal, anti-plant-pathogenic fungi pesticide application. (by machine translation)

Investigation of novel pesticides with insecticidal and antifungal activities: Design, synthesis and SAR studies of benzoylpyrimidinylurea derivatives

In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by 1H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 μg mL?1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 μg mL?1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.

2-amino-6-methoxypyrimidine-4-ol preparation process

The invention discloses a 2-amino-6-methoxypyrimidine-4-ol synthesis process. 4,6-dichloropyrimidine-2-amine is used as a starting material to obtain 2-amino-6-methoxypyrimidine-4-ol through a three-step reaction which includes nucleophilic substitution, electrophilic substitution and catalytic hydrogenation. The synthesis method has advantages of cheapness and easiness in acquisition of raw materials, mild operation conditions, simplicity, convenience and feasibility in aftertreatment and suitableness for industrial application.

POLYMER FILM, RETARDATION FILM, POLARIZING PLATE, LIQUID CRYSTAL DISPLAY, AND COMPOUND

Provided is a polymer film containing at least one of a compound represented by formula (1) of hydrates, solvates, or salts thereof. Y is a methine group or nitrogen atom. Qa, Qb, and Qc are a single bond or a divalent linking group. Ra, Rb, and Rc, are hydrogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group, halogen group, or heterocyclic group. X2 is a single bond or a divalent linking group. X1 is a single bond or a predetermined divalent linking group. R1 and R2 are a hydrogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, or heterocyclic group Formula (1)

DI(HETERO)ARYLAMIDES AND SULFONAMIDES, METHODS FOR THEIR PREPARATION AND THERAPEUTIC USES THEREOF

The present invention refers to compounds of formula (I): as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of conditions associated with the alteration of the activity of β-galactosidase, specially galactosidase beta-1 or GLB1, including GM1 gangliosidoses and Morquio syndrome, type B.

Identification of NVP-BKM120 as a potent, selective, orally bioavailable class i PI3 kinase inhibitor for treating cancer

Phosphoinositide-3-kinases (PI3Ks) are important oncology targets due to the deregulation of this signaling pathway in a wide variety of human cancers. Herein we describe the structure guided optimization of a series of 2-morpholino, 4-substituted, 6-heterocyclic pyrimidines where the pharmacokinetic properties were improved by modulating the electronics of the 6-position heterocycle, and the overall druglike properties were fine-tuned further by modification of the 4-position substituent. The resulting 2,4-bismorpholino 6-heterocyclic pyrimidines are potent class I PI3K inhibitors showing mechanism modulation in PI3K dependent cell lines and in vivo efficacy in tumor xenograft models with PI3K pathway deregulation (A2780 ovarian and U87MG glioma). These efforts culminated in the discovery of 15 (NVP-BKM120), currently in Phase II clinical trials for the treatment of cancer.

PI 3-KINASE INHIBITORS AND METHODS OF THEIR USE

Phosphatidylinositol (PI) 3-kinase inhibitor compounds, their pharmaceutically acceptable salts, and prodrugs thereof; compositions of the new compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier; and uses of the new compounds, either alone or in combination with at least one additional therapeutic agent, in the prophylaxis or treatment of diseases characterized by the abnormal activity of growth factors, protein serine/threonine kinases, and phospholipid kinases, including proliferative diseases, inflammatory and obstructive airways diseases, allergic conditions, auutoimmune and cardiovascular diseases.

PYRIMIDINE DERIVATIVES USED AS PI-3 KINASE INHIBITORS

Phosphatidylinositol (PI) 3-kinase inhibitor compounds (I), their pharmaceutically acceptable salts, and prodrugs thereof ; compositions of the new compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier; and uses of the new compounds, either alone or in combination with at least one additional therapeutic agent, in the prophylaxis or treatment of proliferative diseases characterized by the abnormal activity of growth factors, protein serine/threonine kinases, and phospholipid kinases.

METHOD FOR THE PRODUCTION OF 2-AMINO-4-CHLORO-6-ALKOXYPYRIMIDINES

The invention relates to a method for producing 2-amino-4-chloro-6-alkoxypyrimidines by reacting 2-amino-4,6-dichloropyrimidine with an alkali alcoholate or a mixture of alkali hydroxides and an alcohol in a polar aprotic solvent (mixture), whereupon the solvent is distilled off to > 30 percent and the product is precipitated by adding water during or following the distillation process. The inventive method, in which especially acetone is used as a polar aprotic solvent and which can be carried out at temperatures between 5 and 60 °C, allows 2-amino-4-chloro-6-alkoxypyrimidines and above all 2-amino-4-chloro-6-methoxypyrimidine to be produced in a particularly economical and environmentally friendly manner while obtaining high yields and a very distinctive purity.

Phototransformation of Chlorimuron-ethyl in Aqueous Solution

Chlorimuron-ethyl is relatively stable in water buffered to pH 7.0 and 9.0, but hydrolyzes readily (half-life, 14 d) in water buffered to pH 4.0. In addition, chlorimuron-ethyl photodegrades rapidly and extensively in aqueous solution. The predominant photoproducts are 4-methoxy-6-chloro-2-aminopyrimidine, ethyl 2-aminosulfonylbenzoate, N-(4-methoxy-6-chloropyrimidin-2-yl)methyl urea, and o-benzoic sulfimide (saccharin). A minor deesterified product (chlorimuron) was evident. The decrease in chlorimuron-ethyl concentration in aqueous solutions followed first-order kinetics. The rate of degradation in different types of water followed the order irrigation water > tap water > distilled water. Chlorimuron-ethyl photodegraded in pH 4, 7, and 9 buffer solutions under both UV and sunlight. A faster degradation rate in pH 4.0 buffer solution was observed.