145783-15-9

Basic information

• Product Name: 4,6-dichloro-2-propylthiopyrimidine-5-amine
• Synonyms: 4,6-dichloro-2-propylthiopyrimidine-5-amine;4,6-dichloro-2-(propylthio)-5-PyriMidinaMine;4,6-Dichloro-2-(propylthio)pyrimidin-5-amine;Tecagrelor InterMediate 3;5-PyriMidinaMine, 4,6-dichloro-2-(propylthio)-;4,6-dichloro-2-(propylsulfanyl)-5-pyriMidinaMine;4,6-dichloro-2-(propylsulfanyl)pyriMidin-5-aMine;4,6-Dichloro-2-propylsulfanyl-pyriMidin-5-ylaMine
• CAS NO: 145783-15-9
• Molecular Formula: C₇H₉Cl₂N₃S
• Molecular Weight: 238.13746
• EINECS: 1308068-626-2
• Product Categories: Intermediate of Ticagrelor
• Mol File: 145783-15-9.mol

Chemical Properties

• Boiling Point: 334.05 °C at 760 mmHg
• Flash Point: 155.828 °C
• Appearance: /
• Density: 1.44
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -3.46±0.12(Predicted)
• Water Solubility: 100mg/L at 22℃
• CAS DataBase Reference: 4,6-dichloro-2-propylthiopyrimidine-5-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-dichloro-2-propylthiopyrimidine-5-amine(145783-15-9)
• EPA Substance Registry System: 4,6-dichloro-2-propylthiopyrimidine-5-amine(145783-15-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 145783-15-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,6-dichloro-2-propylthiopyrimidine-5-amine is used as a key intermediate in the synthesis of Ticagrelor, a drug that inhibits platelet aggregation by reversibly blocking the P2Y12 receptor. 4,6-dichloro-2-propylthiopyrimidine-5-amine plays a crucial role in the development of antiplatelet agents for the treatment of cardiovascular diseases, such as acute coronary syndrome and stroke.
Additionally, 4,6-dichloro-2-propylthiopyrimidine-5-amine is utilized in the preparation of other reversible P2Y12 receptor antagonists, which have potential applications in the treatment of various thrombotic disorders and conditions related to blood clotting.

Synthesis

The synthesis of 4,6-dichloro-2-propylthiopyrimidine-5-amine is as follows：tert-Butyl methyl ether (370 g) was placed under nitrogen in a 1 L stainless steel autoclave equipped with a temperature-controlled jacket, an Ekato InterMIG stirrer, an internal temperature sensor and a dip pipe, and 4,6-dichloro-5-nitro-2-propylsulfanyl-pyrimidine (94.5 g, 0.35 mol) was added and dissolved at a stirring rate of 200 min-1. The catalyst suspension was prepared and transferred into the autoclave as described in the preceding example. The autoclave was sealed and the stirring rate was increased to 600 min-1 while the autoclave was purged four times with nitrogen. Subsequently, hydrogen gas feed via the dip pipe at a constant flow rate (pmax=10 bar) as well as a heating-up ramp (45 K/h) from 20° C. to 65° C. were started in parallel, while stirring at 600 min-1. The progress of the exothermic reaction was followed by recording the hydrogen uptake as well as the internal and jacket temperature curve. Upon completion of the hydrogen uptake (ca. 1.1 mol or 3 molar equivalents) after about 4 h, stirring of the reaction mixture was continued for an additional 3 hours at 65° C. After unloading the autoclave (the reactor was cooled down to 20° C., the hydrogen pressure was released and the reactor purged four times with nitrogen), the catalyst was filtered off. The autoclave as well as the filter cake (catalyst) were washed with tent-butyl methyl ether (185 g). The organic phases were combined and the water layer separated. An IPC-sample was taken to analyze the product mixture. The conversion was found to be quantitative with no nitroso or hydroxylamine intermediate being detectable.

InChI:InChI=1/C7H9Cl2N3S/c1-2-3-13-7-11-5(8)4(10)6(9)12-7/h2-3,10H2,1H3

Synthetic route

4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine (145783-14-8) → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
With ammonium molibdate; hydrogen; hypophosphorous acid; platinum on carbon In tert-butyl methyl ether at 20 - 65℃; under 7500.75 Torr; for 7h; Product distribution / selectivity; Inert atmosphere;	100%
Stage #1: 4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine With iron; acetic acid In methanol at 50℃; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;	95%
With iron; acetic acid for 4h;	73%

4,6-dihydroxy-5-amino-2-(propylmercapto)pyrimidine hydrochloride (1549834-66-3) → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
With trichlorophosphate for 22.5h; Time; Concentration; Reflux; Sealed tube;	96%
With trichlorophosphate for 22.5h; Time; Sealed tube; Reflux;	96%
With pyridine; trichlorophosphate at 88 - 92℃; for 24h;	84%

4,6-dihydroxy-2-(propylthio)-5-aminopyrimidine → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; trichlorophosphate at 75℃; for 4h; Reagent/catalyst; Temperature;	93%
With trichlorophosphate for 24h; Reflux; Large scale;	90%

5-amino-2-propylthio-pyrimidine → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
With chlorine In chloroform at 30℃; for 6h;	88%

4,6-dichloro-5-[(E)-2-(4-phenyl)diazenyl]-2-(propylsulfanyl)pyrimidine → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
Stage #1: 4,6-dichloro-5-[(E)-2-(4-phenyl)diazenyl]-2-(propylsulfanyl)pyrimidine With ammonium formate; zinc In methanol; isopropyl alcohol for 0.166667h; Stage #2: With hydrogen; Raney Ni In methanol; isopropyl alcohol at 20℃; under 7500.75 Torr; for 11h; Product distribution / selectivity;	78%

4,6-dichloro-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine (376608-73-0) → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
With hydrogen; 10 wt% platinum on carbon In ethyl acetate at 20 - 40℃; under 2250.23 Torr; for 0.5 - 2.5h; Product distribution / selectivity;
Multi-step reaction with 2 steps 1: ammonium formate; zinc / methanol; isopropyl alcohol / 0.33 h 2: hydrogen / 11 h / 20 °C View Scheme

4,6-dichloro-5-[(E)-2-(4-phenyl)diazenyl]-2-(propylsulfanyl)pyrimidine → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + C19H18ClN5S

Conditions	Yield
With hydrogen; platinum on carbon In methanol; isopropyl alcohol at 20℃; under 4500.45 Torr; for 32h;

4,6-dihydroxy-2-(propylsulfanyl)pyrimidine (145783-12-6) → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium acetate; sodium hydroxide / ethanol; water / 20 °C 1.2: 0.5 h / 0 °C 1.3: 0 - 5 °C 2.1: pyridine; trichlorophosphate / toluene / 4.75 h / 70 °C 3.1: ammonium formate; zinc / methanol; isopropyl alcohol / 0.33 h 4.1: hydrogen / 11 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: nitric acid; acetic acid / 55 °C 2: trichlorophosphate / N,N-dimethyl acetamide / Reflux 3: ammonia View Scheme
Multi-step reaction with 3 steps 1: nitric acid; acetic acid / 2 h / Cooling with ice 2: dmap; trichlorophosphate / 5 h / Reflux 3: iron; acetic acid / methanol / 2 h / Reflux View Scheme

4,6-dihydroxy-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine (376608-72-9) → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; trichlorophosphate / toluene / 4.75 h / 70 °C 2: ammonium formate; zinc / methanol; isopropyl alcohol / 0.33 h 3: hydrogen / 11 h / 20 °C View Scheme

C14H16Cl2N4S → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
With hydrogen at 20℃; for 11h;

5-tert-butoxycarbonyl-amino-2-propyl-thio-pyrimidine-4,6-diol → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; trichlorophosphate at 90℃; for 5h;	157 mg

N-(4,6-dihydroxy-2-(propylthio)pyrimidin-5-yl)acetamide (1549834-56-1) → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / methanol / 18 h / 50 °C 2: trichlorophosphate / 22.5 h / Sealed tube; Reflux View Scheme

5-chloro-2-propylthio-pyrimidine → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / dichloromethane / 8 h / 30 °C 2: chlorine / chloroform / 6 h / 30 °C View Scheme

4,6-dihydroxy-5-nitro-2-(propylthio)pyrimidine (145783-13-7) → 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate / N,N-dimethyl acetamide / Reflux 2: ammonia View Scheme
Multi-step reaction with 2 steps 1: dmap; trichlorophosphate / 5 h / Reflux 2: iron; acetic acid / methanol / 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: trichlorophosphate / 2 h / Reflux 2: acetic acid; iron / methanol / 20 °C / Reflux View Scheme

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + trifluoroacetic anhydride (407-25-0) → C9H8Cl2F3N3OS

Conditions	Yield
With triethylamine In dichloromethane at 10 - 20℃; for 1h;	96%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + methylamine (74-89-5) → 6-chloro-N4-methyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 1h; Sealed tube;	96%
In methanol at 100℃; for 1h; Sealed tube;	96%
In methanol for 1h; Sealed tube;	96%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + cyclobutylamine (2516-34-9) → 6-chloro-N4-cyclobutyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 1h; Sealed tube;	96%
In methanol at 100℃; for 1h; Sealed tube;	96%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + 1-pentanamine (110-58-7) → 6-chloro-N4-pentyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 0.5h; Sealed tube;	96%
In methanol at 100℃; for 0.5h; Sealed tube;	96%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (274693-55-9) → 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol

Conditions	Yield
Stage #1: 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine; [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol In water; N,N-dimethyl-formamide for 0.333333h; Stage #2: With triethylamine at 20℃; Reflux;	95%
With N-ethyl-N,N-diisopropylamine at 120 - 125℃; for 10h; Temperature; Inert atmosphere;	93.5%
With sodium hydrogencarbonate In water at 100℃; for 20h; Reagent/catalyst; Temperature;	88.3%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + Cyclopentamine (1003-03-8) → 6-chloro-N4-cyclopentyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 2h; Sealed tube;	95%
In methanol at 100℃; for 2h; Sealed tube;	95%
In methanol Sealed tube;	95%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + isopropylamine (75-31-0) → 6-chloro-N4-isopropyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 1.5h; Sealed tube;	95%
In methanol at 100℃; for 1.5h; Sealed tube;	95%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + N-butylamine (109-73-9) → N4-butyl-6-chloro-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 0.5h; Sealed tube;	95%
In methanol at 100℃; for 0.5h; Sealed tube;	95%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + 2-[[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol hydrochloride → 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol

Conditions	Yield
With sodium hydrogencarbonate In water at 85℃; Large scale;	95%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (2R,3R)-2,3-dihydroxybutanedioic acid (376608-65-0) → 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In sulfolane at 107℃; for 3h; Large scale;	94.75%
With sodium hydroxide In ethyl acetate at 90℃; for 20h; Temperature;	90.4%
With sodium hydrogencarbonate In water at 87℃; Temperature; Large scale;	90%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + pentafluorophenyl trifloroacetate (14533-84-7) → C9H8Cl2F3N3OS

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 10 - 20℃; for 5h;	93%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + Cyclopropylamine (765-30-0) → 6-chloro-N4-cyclopropyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 0.5h; Sealed tube;	92%
In methanol at 100℃; for 0.5h; Sealed tube;	92%
With triethylamine In ethanol at 120℃; for 30h;

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + 1-amino-2-propene (107-11-9) → N4-aIIyI-6-chloro-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 0.5h; Sealed tube;	92%
In methanol at 100℃; for 0.5h; Sealed tube;	92%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (155899-66-4) → (3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (220241-60-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 16h;	91%
In methanol at 100℃; for 12h; Sealed tube;	90%
In methanol at 100℃; for 12h; Sealed tube;	90%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + benzylamine (100-46-9) → N4-benzyl-6-chloro-2-propylsulfanyl-pyrimidine-4,5-diamine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	91%
With triethylamine In ethanol for 48h; Reflux;
With triethylamine In ethanol for 48h; Reflux;

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + (tert-butyl (1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate (1350749-64-2) → C21H25ClF2N4O2S

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -85 - -75℃; for 2h; Inert atmosphere;	91%

propylamine (107-10-8) + 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) → 6-chloro-N4-propyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 0.5h; Sealed tube;	91%
In methanol at 100℃; for 0.5h; Sealed tube;	91%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + cyclohexylamine (108-91-8) → 6-chloro-N4-cyclohexyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 1h; Sealed tube;	91%
In methanol at 100℃; for 1h; Sealed tube;	91%
With triethylamine In ethanol at 120℃; for 30h;	90%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + 2-[[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol L-tartrate → 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol

Conditions	Yield
With sodium hydrogencarbonate In water at 90℃; Large scale;	89.4%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + (3aS,4R,6S,6aR)-6-(2-(tert-butoxy)ethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine (1402735-41-4) → C21H35ClN4O4S

Conditions	Yield
With triethylamine In ethanol at 100 - 130℃; Sealed tube; Inert atmosphere;	89%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + C4H6O6*C28H33NO4 → C35H41ClN4O4S

Conditions	Yield
With triethylamine In isopropyl alcohol at 80℃; for 30h; Time; Industrial scale;	89%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + (1S,2S,3R,5S)-3-amino-5-(2-hydroxyethoxy)cyclopentane-1,2-diol (1444301-60-3) → (1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol (1402150-32-6)

Conditions	Yield
With triethylamine at 75℃; for 48h; Concentration; Reagent/catalyst; Temperature; Time;	88%
With triethylamine at 75℃; for 48h; Reagent/catalyst; Time; Temperature;	88%
With triethylamine In methanol; water at 100℃; for 40h;	14.5 g

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + C15H29NO5 → C21H35ClN4O5S

Conditions	Yield
With triethylamine In ethanol at 100 - 130℃; Sealed tube; Inert atmosphere;	88%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + C15H27NO5 → C22H35ClN4O5S

Conditions	Yield
With triethylamine In ethanol at 100 - 130℃; Sealed tube; Inert atmosphere;	88%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + tert-butylamine (75-64-9) → N4-(tert-butyl)-6-chloro-2-(propylthio)pyrimidine-4,5-diamine

Conditions	Yield
In methanol at 100℃; for 24h; Sealed tube;	88%
In methanol at 100℃; for 24h; Sealed tube;	88%

4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine (145783-15-9) + C12H23NO5 → C19H31ClN4O5S

Conditions	Yield
With triethylamine In ethanol at 100 - 130℃; Sealed tube; Inert atmosphere;	87%

Upstream product

• 376608-73-0 4,6-dichloro-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine 
• 145783-14-8 4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine 
• 946855-77-2 4,6-dichloro-5-[(E)-2-(4-phenyl)diazenyl]-2-(propylsulfanyl)pyrimidine 
• 376608-72-9 4,6-dihydroxy-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine 
• 1549834-66-3 4,6-dihydroxy-5-amino-2-(propylmercapto)pyrimidine hydrochloride 
• 145783-13-7 4,6-dihydroxy-5-nitro-2-(propylthio)pyrimidine 
• 1549834-56-1 N-(4,6-dihydroxy-2-(propylthio)pyrimidin-5-yl)acetamide 
• 145783-12-6 4,6-dihydroxy-2-(propylsulfanyl)pyrimidine 

Downstream Products

• 376608-74-1 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol 
• 640285-17-2 6-chloro-N~4~-(4-chlorophenyl)-2-(propylthio)pyrimidine-4,5-diamine 
• 376608-75-2 2-({(3aR,4S,6R,6aS)-6-[7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-yl]-2,2-dimethyltetrahydro-3aH-cyclopentadiene[d][1,3]dioxolene-4-yl}oxy)ethanol 
• 274693-27-5 ticagrelor 
• 220347-05-7 AR-C₁₂₄₉₁₀XX 
• 274693-49-1 (3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 1381841-46-8 2-((1S,2S,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl)oxy)ethyl isobutyl carbonate 
• 1381841-52-6 (1S,2S,3S,4R)-4-(7-((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl butyrate 
• 1381841-55-9 (1S,2S,3S,4R)-4-(7-((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl ethyl carbonate 
• 1381841-56-0 (1S,2S,3S,4R)-4-(7-((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl isobutyl carbonate 
• 274693-26-4 [3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol 
• 1381841-39-9 2-((1S,2S,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl)oxy)ethyl butyrate 
• 220241-60-1 (3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 1402150-28-0 N-[4,6-dichloro-2-(propylthio)pyrimidin-5-yl]formamide 

Relevant articles and documents

Synthesis method of 4,6-dichloro-2-propylmercapto-5-aminopridine

The invention discloses a synthesis method of 4,6-dichloro-2-propylmercapto-5-aminopridine. The synthesis method comprises the following synthesis steps: (1) dissolving diethyl aminomalonate with a protecting group and thiourea in an organic solvent, and conducting reacting under the catalysis of alkali to obtain a compound 1; (2) dissolving the compound 1 in a sodium hydroxide or potassium hydroxide solution, adding an organic solvent, then adding bromopropane into the mixed solvent, and carrying out a propane alkylation reaction to obtain a compound 2; (3) removing an amino protecting group from the compound 2 to obtain a compound 3; and (4) adding organic alkali and a chlorination reagent into the compound 3 for a chlorination reaction to obtain a target compound 4. The synthesis method disclosed by the invention has the advantages of high propane alkylation reaction selectivity, no need for a high-risk nitration reaction, no need for a metal reduction nitro reaction producing high content of solid waste, no need for a high-cost metal catalytic hydrogenation step, cheap and easily available equipment and suitability for industrial production.

Preparation method of ticagrelor intermediate

The invention provides a preparation method as shown in a formula I shown in the specification, especially, a preparation method of 4, 6-dichloro-2-(propylthio)-5-aminopyrimidine. The invention provides a novel method for preparing the ticagrelor intermediate.

Pyrimido triazole compound and medical application thereof (by machine translation)

The present invention relates to a compound of general (I) or a hydrate thereof or a pharmaceutically acceptable salt, thereof, a hydrate thereof or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the same or a pharmaceutically acceptable salt thereof, and use, of the compound or a pharmaceutically acceptable salt thereof in the manufacture of a medicament . The medicament is for anti-platelet aggregation and treatment of related diseases such as antithrombotic . (by machine translation)

Purification method of 4,6-dichloro-2-(thiopropyl)-5-aminopyrimidine

The invention discloses a purification method of 4,6-dichloro-2-(thiopropyl)-5-aminopyrimidine. The method comprises steps including oil removal, salification, dissociation and recrystallization purification of a crude 4,6-dichloro-2-(thiopropyl)-5-aminopyrimidine product to finally obtain high-purity 4,6-dichloro-2-(thiopropyl)-5-aminopyrimidine. The purification method disclosed by the inventionis simple and convenient to operate, high in yield and suitable for large-scale production.

Synthesis method of ticagrelor intermediate

The invention provides a synthesis method of a ticagrelor intermediate 1. By selecting a more stable amino protecting group, the formation of by-products in the cyclization step is favorably controlled, the reaction conditions in each step are mild, the conversion rate is higher, the cost is effectively reduced, and the method is suitable for industrial production.

Design, synthesis and in vitro biological evaluation of novel [1,2,3]triazolo[4,5-d]pyrimidine derivatives containing a thiosemicarbazide moiety

A series of hybrid molecules containing [1,2,3]triazolo[4,5-d]pyrimidine and thiosemicarbazide moieties were designed, synthesized and evaluated for their antiproliferative activities against MGC-803, NCI-H1650 and PC-3 human cancer cells. Some of the synthesized compounds showed moderate to good activity against three selected cancer cell lines. Among these compounds, compound 29 displayed the most potent antiproliferative activity as well as good selectivity between cancer cells and normal cells. Further mechanism studies revealed that compound 29 could obviously inhibit the colony formation and migration of MGC-803 as well as induced apoptosis.

Synthesis, Antiplatelet Aggregation Activity Evaluation and 3D-QSAR of a Series of Novel 6-Alkylamino(Alkoxyl)-2-Propylthio-8-Azapurine Nucleosides

A series of novel 6-alkylamino(alkoxyl)-2-propylthio-8-azapurine nucleosides were synthesized by an improved route, and the human antiplatelet aggregation activities of these new compounds were evaluated. A self-organizing molecular field analysis method was used to study the three-dimensional quantitative structure–activity relationship of these novel nucleosides. The results of the antiplatelet aggregation activity evaluation and analysis of the self-organizing molecular field analysis models through shape and electrostatic grids may provide a basis for the development of new and potent antiplatelet agents.

Pyrimidine and triazole containing LSD1 inhibitor and preparation method and application thereof

The invention belongs to the field of medicinal chemistry, and discloses a pyrimidine and triazole containing compound and a preparation method and application thereof in preparation of anti-cancer medicine with lysine specific demethylase 1 (LSD1) being a target. The general formula of the compound is shown in the drawing I. In-vitro LSD1 enzyme inhibition activity experiments prove that by inhibiting LSD1 activity, the compound has obvious inhibiting and killing effects on kinds of cancer cells and can be applied to preparation of the anti-cancer medicine as a further developed lead compound.

Design, synthesis and antiproliferative activity of thiazolo[5,4-d]pyrimidine derivatives through the atom replacement strategy

A series of thiazolo[5,4-d]pyrimidine derivatives were designed through the atom replacement strategy based on biologically validated scaffolds and then evaluated for their antiproliferative activities on cancer cell lines. The structure-activity relationship studies were conducted, leading to the identification of compound 22, which exhibited good antiproliferative activity against HGC-27 with an IC50 value of 1.22 μM and low toxicity against GES-1 cells. Mechanistic studies showed that compound 22 inhibited the colony formation and migration of HGC-27 as well as induced apoptosis. The western blot experiments proved that compound 22 up-regulated expression of Bax, down-regulated expression levels of Bcl-2 and cleaved caspased-3/9. These findings indicate that compound 22 may serve as a template for designing new agents for the treatment of human gastric cancers. The atom replacement strategy could be viable strategy for designing new anticancer drugs and may find its applications in drug design.

Design, synthesis, and biological evaluation of new thiazolo[5,4-: D] pyrimidine derivatives as potent antiproliferative agents

A series of thiazolo[5,4-d]pyrimidine derivatives were synthesized and evaluated for their antiproliferative activities against several human cancer cell lines. Structure-activity relationship studies were carried out, showing that most of the target compounds had good inhibition against the tested cell lines. Among them, compound 7i exhibited potent inhibition against human gastric cancer cells MGC-803 and HGC-27 with IC50 values of 4.64 and 5.07 μM, respectively and around 12-fold selectivity between MGC-803 and GES-1, indicating a relatively low toxicity to normal cells. The potency and low toxicity of compound 7i make the thiazolo[5,4-d]pyrimidine an attractive scaffold for designing new derivatives selectively targeting MGC-803 cells.