2-(((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-yl)oxy)ethanol

Base Information

• Chemical Name: 2-(((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-yl)oxy)ethanol
• CAS No.: 376608-74-1
• Molecular Formula: C17H27ClN4O4S
• Molecular Weight: 418.93900
• European Community (EC) Number: 468-100-0
• DSSTox Substance ID: DTXSID901101032
• Nikkaji Number: J2.688.088B
• Wikidata: Q76415262
• Mol file: 376608-74-1.mol

Synonyms:376608-74-1;2-(((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-yl)oxy)ethanol;Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-;2-(((3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethan-1-ol;2-[[(3aR,4S,6R,6aS)-6-[(5-amino-6-chloro-2-propylsulfanylpyrimidin-4-yl)amino]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]ethanol;2-[[(3aR,4S,6R,6aS)-6-[[5-Amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-;Ticagrelor intermediate 12;MFCD21362979;2-(((3aR,4S,6R,6aS)-6-((5-Amino-6-chloro-2-(propylsulfanyl)-4,5-dihydropyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3ah-cyclopenta(d)(1,3)dioxol-4-yl)oxy)ethanol;2-(((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-yl)oxy)ethanol;2-[((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-yl)oxy]ethanol;2-{[(3aR,4S,6R,6aS)-6-{[5-amino-6-chloro-2-(propylsulfanyl)-4,5-dihydropyrimidin-4-yl]amino}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy}ethanol;2-{[(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-yl]oxy}ethanol;SCHEMBL2131051;AMY3293;LODREYVWDWCAOB-RSLMWUCJSA-N;DTXSID901101032;UL125;CS-M2084;AKOS025396335;DS-8562;EC 468-100-0;EN300-7415184;A854854;2-((3aR,4S,6R,6aS)-6-(5-Amino-6-chloro-2-(propylthio)pyrimidin-4-ylamino)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol;2-[((3 aR,4S,6R,6aS)-6-{[5-Amino-6-chloro-2-(propylthio)pyrimidin-4-yl]amino}-2,2-dimethyltetrahydro-3 aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]ethanol;2-[((3aR,4S,6R,6aS)-6-{[5-Amino-6-chloro-2-(propylthio)pyrimidin-4-yl]amino}-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]ethanol;2-[[(3aR,4S,6R,6aS)-6-[[5-Amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol;2-{[(3aR,4S,6R,6aS)-6-{[5-amino-6-chloro-2-(propylsulfanyl)pyrimidin-4-yl]amino}-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]oxy}ethan-1-ol;6-Chloro-4-[[(1R,5S,6R,8S)-8-(2-hydroxyethoxy)-3,3-dimethyl-2,4-dioxabicyclo[3.3.0]octane-6-yl]amino]-2-(propylthio)pyrimidine-5-amine

Chemical Property of 2-(((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-yl)oxy)ethanol

Chemical Property:

• Appearance/Colour: Off-White Solid
• Melting Point: 85-88°C
• Boiling Point: 598.9±50.0 °C(Predicted)
• PKA: 14.33±0.10(Predicted)
• PSA: 140.28000
• Density: 1.37±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• LogP: 2.29920
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 35mg/L at 22℃
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 418.1441542
• Heavy Atom Count: 27
• Complexity: 492

Purity/Quality:

2-[[(3aR,4S,6R,6aS)-6-[[5-Amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCSC1=NC(=C(C(=N1)Cl)N)NC2CC(C3C2OC(O3)(C)C)OCCO
• Isomeric SMILES: CCCSC1=NC(=C(C(=N1)Cl)N)N[C@@H]2C[C@@H]([C@@H]3[C@H]2OC(O3)(C)C)OCCO
• Uses: 2-[[(3aR,4S,6R,6aS)-6-[[5-Amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol is used as a reagent in the synthesis of Ticagrelor (T437700) derivatives as antiplatelet agents.

Technology Process of 2-(((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-yl)oxy)ethanol

There total 31 articles about 2-(((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-yl)oxy)ethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

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 (376608-74-1)

Guidance literature:

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;

With triethylamine; at 20 ℃; Reflux;

Reference yield: 95.0%

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 (376608-74-1)

Guidance literature:

With sodium hydrogencarbonate; In water; at 85 ℃; Large scale;

Reference yield: 94.75%

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 (376608-74-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In sulfolane; at 107 ℃; for 3h; Large scale;

upstream raw materials:

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

2-[[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol oxalate

4,6-dihydroxy-2-(propylsulfanyl)pyrimidine

Downstream raw materials:

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

ticagrelor

C₂₃H₂₈F₂N₆O₅S

C₁₇H₂₄ClN₅O₄S

Refernces

• 1、 -. "NEW USE OF TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES". Page/Page column 13; 15. . Retrieved 2021/01/29.
• 2、 Goffin, Eric,Jacques, Nicolas,Lancellotti, Patrizio,Musumeci, Lucia,Nchimi, Alain,Pirotte, Bernard,Oury, Cécile. "Synthesis of ticagrelor analogues belonging to 1,2,3-triazolo[4,5-d]pyrimidines and study of their antiplatelet and antibacterial activity". . . Retrieved 2020/09/11.