(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

white powde

Uses

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

Synthesis

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(14047-28-0)Related Product Information

• Hydroxypropyl cellulose
• 6-Benzylaminopurine
• Tribenuron methyl
• Ethanol
• Hydroxypropyl methyl cellulose
• 2-Hydroxypropyl-β-cyclodextrin
• METSULFURON METHYL
• 3-METHYLADENINE
• Starch, hydrogen phosphate, 2-hydroxypropyl ether
• Hydroxypropyl starch
• Methyl salicylate
• Ethyl acetate
• Adenine
• Purine
• Kresoxim-methyl
• N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine
• Thiophanate-methyl
• isopropyl ((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-D-alaninate