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14047-28-0

14047-28-0 Structure

14047-28-0 Structure
IdentificationBack Directory
[Name]

(R)-(+)-9-(2-Hydroxypropyl)adenine
[CAS]

14047-28-0
[Synonyms]

Tenofovir Impurity 24
(R)-9-(2-Hydroxypropyl)ademine
9-[(2R)-2-Hydroxypropyl]adenine
D-(-)-9-(2-Hydroxypropyl)adenine
(R)-(+)-9-(2-Hydroxypropyl)adenine
R-9-(2-hydroxypropyl) adenine, 9-HPA
(R)-9-(2-hydroxypropyl) adenine (SC)
(R)-9-(2-Hydroxypropyl)adenine
(2R)-1-(6-Aminopurin-9-yl)propan-2-ol
(R)-1-(6-AMino-purin-9-yl)-propan-2-ol
(R)-(+)-9-(2-HYDROXYPROPYL)ADENINE,98%
(R)-(+)-9-(2-Hydroxypropyl)adenine(PMP)
(R)-(+)-9-(2-Hydroxypropyl)adenine (HPA)
6-Amino-alpha-methyl-9H-purine-9-ethanol
(αR)-6-AMino-α-Methyl-9H-purine-9-ethanol
(2R)-1-(6-aMino-9H-purin-9-yl)propan-2-ol
9H-Purine-9-ethanol,6-amino-a-methyl-, (aR)-
(R)-6-aMino-alpha-Methyl-9H-purine-9-ethanol
(R)-6-aMino-alpha-Methyl-9H-purine-9-ethanol (HPA)
(R)-9-[2-(Hydroxypropyl] Adenine (Desphosphoryl Tenofovir)
[EINECS(EC#)]

604-188-0
[Molecular Formula]

C8H11N5O
[MDL Number]

MFCD07369451
[MOL File]

14047-28-0.mol
[Molecular Weight]

193.21
Chemical PropertiesBack Directory
[Appearance]

white powde
[Melting point ]

193 °C
[Boiling point ]

457.7±55.0 °C(Predicted)
[density ]

1.57
[storage temp. ]

-20°C Freezer
[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|
Hazard InformationBack Directory
[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]

6H-Purin-6-imine, 1,7-dihydro- (9CI)

66224-66-6

(R)-(+)-Propylene carbonate

16606-55-6

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

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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
[HS Code ]

2933.99.8290
Spectrum DetailBack Directory
[Spectrum Detail]

(R)-(+)-9-(2-Hydroxypropyl)adenine(14047-28-0)1HNMR
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