4,6-Dichloro-2-(propylthio)pyrimidin-5-amine supplier

Name
4,6-dichloro-2-propylthiopyrimidine-5-amine
EINECS 808-051-8
CAS No. 145783-15-9
Article Data28
CAS DataBase
Density 1.445 g/cm³
Solubility 100mg/L at 22℃
Melting Point
Formula C₇H₉Cl₂N₃S
Boiling Point 334.05 °C at 760 mmHg
Molecular Weight 238.141
Flash Point 155.828 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4,6-dichloro-2-propylthiopyrimidine-5-amine;5-amino-4,6-dichloro-2-propylthiopyrimidine;EX-7178;5-Amino-4,6-dichloro-2-(propylthio)pyrimidine;
PSA 77.10000
LogP 3.44890

Synthetic route

: 145783-14-8
4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine

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

Conditions

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%

: 1549834-66-3
4,6-dihydroxy-5-amino-2-(propylmercapto)pyrimidine hydrochloride

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

Conditions

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

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

Conditions

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

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

Conditions

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

: 4,6-dichloro-5-[(E)-2-(4-phenyl)diazenyl]-2-(propylsulfanyl)pyrimidine

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

Conditions

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%

: 376608-73-0
4,6-dichloro-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine

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

Conditions

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

A: 145783-15-9
4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine

B: C19H18ClN5S

Conditions

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

: 145783-12-6
4,6-dihydroxy-2-(propylsulfanyl)pyrimidine

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

Conditions

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

: 376608-72-9
4,6-dihydroxy-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine

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

Conditions

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

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

Conditions

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

: 5-tert-butoxycarbonyl-amino-2-propyl-thio-pyrimidine-4,6-diol

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

Conditions

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

: 1549834-56-1
N-(4,6-dihydroxy-2-(propylthio)pyrimidin-5-yl)acetamide

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

Conditions

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

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

Conditions

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

: 145783-13-7
4,6-dihydroxy-5-nitro-2-(propylthio)pyrimidine

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

Conditions

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

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

: 407-25-0
trifluoroacetic anhydride

: C9H8Cl2F3N3OS

Conditions

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

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

: 74-89-5
methylamine

: 6-chloro-N4-methyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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%

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

: 2516-34-9
cyclobutylamine

: 6-chloro-N4-cyclobutyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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

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

: 110-58-7
1-pentanamine

: 6-chloro-N4-pentyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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

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

: 274693-55-9
[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

: 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

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%

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

: 1003-03-8
Cyclopentamine

: 6-chloro-N4-cyclopentyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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%

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

: 75-31-0
isopropylamine

: 6-chloro-N4-isopropyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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

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

: 109-73-9
N-butylamine

: N4-butyl-6-chloro-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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

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

: 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

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

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

: 376608-65-0
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

: 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

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%

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

: 14533-84-7
pentafluorophenyl trifloroacetate

: C9H8Cl2F3N3OS

Conditions

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

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

: 765-30-0
Cyclopropylamine

: 6-chloro-N4-cyclopropyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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;

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

: 107-11-9
1-amino-2-propene

: N4-aIIyI-6-chloro-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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

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

: 155899-66-4
(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

: 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

Conditions

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%

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

: 100-46-9
benzylamine

: N4-benzyl-6-chloro-2-propylsulfanyl-pyrimidine-4,5-diamine

Conditions

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;

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

: 1350749-64-2
(tert-butyl (1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate

: C21H25ClF2N4O2S

Conditions

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

: 107-10-8
propylamine

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

: 6-chloro-N4-propyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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

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

: 108-91-8
cyclohexylamine

: 6-chloro-N4-cyclohexyl-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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%

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

: 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

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

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

: 1402735-41-4
(3aS,4R,6S,6aR)-6-(2-(tert-butoxy)ethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

: C21H35ClN4O4S

Conditions

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

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

: C4H6O6*C28H33NO4

: C35H41ClN4O4S

Conditions

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

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

: 1444301-60-3
(1S,2S,3R,5S)-3-amino-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

: 1402150-32-6
(1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

Conditions

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

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

: C15H29NO5

: C21H35ClN4O5S

Conditions

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

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

: C15H27NO5

: C22H35ClN4O5S

Conditions

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

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

: 75-64-9
tert-butylamine

: N4-(tert-butyl)-6-chloro-2-(propylthio)pyrimidine-4,5-diamine

Conditions

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

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

: C12H23NO5

: C19H31ClN4O5S

Conditions

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

4,6-Dichloro-2-(propylthio)pyrimidin-5-amine Specification

The CAS registry number of 5-Pyrimidinamine, 4,6-dichloro-2-(propylthio)- is 145783-15-9. This chemical is also known as 4,6-Dichloro-2-propylthiopyrimidine-5-amine. The molecular formula of it is C₇H₉Cl₂N₃S and molecular weight is 238.13746. Its systematic name and IUPAC name are the same which is called 4,6-dichloro-2-(propylsulfanyl)pyrimidin-5-amine.

Physical properties about this chemical are: (1)ACD/LogP: 3.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4; (4)ACD/LogD (pH 7.4): 4; (5)ACD/BCF (pH 5.5): 942; (6)ACD/BCF (pH 7.4): 942; (7)ACD/KOC (pH 5.5): 4680; (8)ACD/KOC (pH 7.4): 4680; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.615; (13)Molar Refractivity: 57.523 cm³; (14)Molar Volume: 164.803 cm³; (15)Surface Tension: 65.883 dyne/cm; (16)Density: 1.445 g/cm³; (17)Flash Point: 155.828 °C; (18)Enthalpy of Vaporization: 57.697 kJ/mol; (19)Boiling Point: 334.05 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1nc(SCCC)nc(Cl)c1N
(2)InChI: InChI=1/C7H9Cl2N3S/c1-2-3-13-7-11-5(8)4(10)6(9)12-7/h2-3,10H2,1H3
(3)InChIKey: CJJLJBFJNXMANZ-UHFFFAOYAU

Product Name

4,6-dichloro-2-propylthiopyrimidine-5-amine

Synthetic route

4,6-Dichloro-2-(propylthio)pyrimidin-5-amine Specification

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