(R)-(+)-9-(2-Hydroxypropyl)adenine CAS 14047-28-0

Introduction：Basic information about (R)-(+)-9-(2-Hydroxypropyl)adenine CAS 14047-28-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(R)-(+)-9-(2-Hydroxypropyl)adenine Basic information

• Product Name: (R)-(+)-9-(2-Hydroxypropyl)adenine
• Synonyms: R-9-(2-hydroxypropyl) adenine, 9-HPA;(R)-(+)-9-(2-HYDROXYPROPYL)ADENINE,98%;(R)-(+)-9-(2-Hydroxypropyl)adenine;6-Amino-alpha-methyl-9H-purine-9-ethanol;Tenofovir (R)-Propanol Impurity;D-(-)-9-(2-Hydroxypropyl)adenine;(R)-9-[2-(Hydroxypropyl] Adenine(Desphosphoryl Tenofovir);(R)-6-aMino-alpha-Methyl-9H-purine-9-ethanol
• CAS: 14047-28-0
• MF: C8H11N5O
• MW: 193.21
• EINECS: 604-188-0
• Product Categories: Tenofovir;Chiral Reagents;Bases & Related Reagents;Nucleotides
• Mol File: 14047-28-0.mol

(R)-(+)-9-(2-Hydroxypropyl)adenine Chemical Properties

• Melting point: 193 °C
• Boiling point: 457.7±55.0 °C(Predicted)
• density: 1.57
• storage temp.: Keep in dark place,Inert atmosphere,2-8°C
• solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly, Heated)
• form: Solid
• pka: 14.42±0.20(Predicted)
• color: White to Off-White
• InChI: InChI=1/C8H11N5O/c1-5(14)2-13-4-12-6-7(9)10-3-11-8(6)13/h3-5,14H,2H2,1H3,(H2,9,10,11)/t5-/s3
• InChIKey: MJZYTEBKXLVLMY-GQMHJJTINA-N
• SMILES: N1(C[C@@H](C)O)C=NC2C(=NC=NC1=2)N |&1:2,r|

Safety Information

• HS Code: 2933.99.8290

(R)-(+)-9-(2-Hydroxypropyl)adenine Usage And Synthesis

Chemical Properties

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Uses

(R)-9-[2-(Hydroxypropyl] Adenine (Desphosphoryl Tenofovir) (cas# 14047-28-0) is a useful reagent for preparing the antiviral drug tenofovir.

Synthesis

66224-66-6

16606-55-6

14047-28-0

To a reaction flask was added 200 mL of N,N-dimethylformamide (DMF) protected by N2, adenine (30.0 g, 0.222 mol, 1 equiv) and stirred. NaOH (0.45 g, 0.011 mol) and R-propylene carbonate (28.5 g, 0.279 mol, 1.26 eq.) were subsequently added. The reaction mixture was warmed to 130-140 °C within 12 h of the sampling test, and the reaction was stopped when the adenine content dropped to 1% or less. Slowly cooled to below 90°C, 200 mL of toluene was added, cooling was continued to 0-5°C, and the mixture was stirred for 2 hours. Filtered and dried to give 38.13 g white solid in 87% yield.

References

[1] Patent: CN103848869, 2016, B. Location in patent: Paragraph 0053; 0054
[2] Patent: CN103848868, 2017, B. Location in patent: Paragraph 0055; 0058; 0059
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 26, p. 7799 - 7806
[4] Patent: WO2008/56264, 2008, A2. Location in patent: Page/Page column 69-70; 75; 81
[5] Patent: WO2015/51874, 2015, A1. Location in patent: Page/Page column 6; 20; 21

(R)-(+)-9-(2-Hydroxypropyl)adenine Preparation Products And Raw materials

• Raw materials: 6H-Purin-6-imine, 1,7-dihydro- (9CI)-->Adenine-->(R)-1-(6-chloro-9H-purin-9-yl)propan-2-ol-->Tenofovir Disoproxil Related Compound B (10 mg) ((E)-9-(Prop-1-enyl)-9H-purin-6-amine)-->(R)-(+)-Propylene oxide-->(R)-(+)-Propylene carbonate-->N,N-Dimethylformamide-->Sodium hydroxide