Certificate of Analysis

BDG Synthesis certiIies that this reIerence material meets or exceeds the speciIications stated herein.

Barry R. Dent, PhD, Director
11 February 2010
Name: -Desmethylsildenafil
CAS Number: 137-82-1
Structure:

Molecular Weight:
21
H
28
N

O
4
S 40.
Lot Number: BDG 4434
Appearance: White, crystalline solid
Corrected Purity: .1 (HPL) - 3.3 (water) .8
Re-test Date: 11 February 2011
Storage and Handling: Temperature: ambient laboratory temperature; may be reIrigerated.
Humidity: may be hygroscopic; store desiccated; recommended to determine
water content periodically.
Light: protect Irom strong sunlight.
aution: only experienced laboratory personnel should handle the material.
Version 2 1/
Identity and Purity
Proton NMR Spectrum
Identity: the signals are consistent with the proposed structure and in accord with literature where available.
Residual Solvents: no residual solvents are observed.
Impurities: no signiIicant impurities are evident in the spectrum.
Carbon-13 NMR Spectrum
Identity: the signals are consistent with the proposed structure and in accord with literature where available.
High-resolution Mass Spectrum (ESI+
Found 461.1977.
21

29
N
6
O
4
S M

requires 461.1971. The deviation oI 1. ppm is within normally

accepted limits Ior the establishment oI identity by RMS.
HPLC
A sharp, slightly tailing peak is observed (99.1 ). Note: in the absence oI reIerence materials Ior preparing
calibration curves, it is assumed that all peaks have the same detector response. Where possible, the conditions oI
analysis Iollow a pharmacopeial or literature method, or have been adapted Irom same.
Elemental nalysis
Found: 5.41, 6.4, N 17.86

21

28
N
6
O
4
S0.5
2
O Requires: 5.72, 6.2, N 17.90

21

28
N
6
O
4
S Requires: 54.77, 6.1, N 18.25
The elemental analyses Iall somewhat outside those expected Ior anhydrous material; the presence oI water is
reasonably expected Irom the method oI puriIication and/or the type oI material, and the 'best-Iit hydrated
molecular Iormula is given.
Karl-Fischer nalysis
Found:
2
O .

21

28
N
6
O
4
S0.5
2
O Requires:
2
O 1.9
OI necessity, only a small sample could be used and only a single or duplicate analysis perIormed. We are unable to
state what the errors in the reported water content are, but recommend that the result be used, as the best available,
when determining corrected purity.
The available quantity oI custom-synthesised material is always small, and this limits the extent and type oI analytical data
which can be obtained. This ertiIicate is presented in descriptive Iormat Ior use by analytical chemists who are trained in the
use oI custom-synthesised materials. ustom materials oIten contain higher levels oI residual solvents and/or water, and we
urge you to use the corrected purity where needed rather than the raw P purity. This compound is intended Ior use as an
analytical reIerence material and it is not Ior human administration. Structures are shown with relative stereochemistry unless
otherwise speciIied.
The re-test date is assigned Irom experience gained with the material in the laboratory and/or on storage. It is not possible to
perIorm Iormal storage studies because oI the small amount oI material available.
2/5
11 22 33 44 55 66 77 8 8 9 9 10 10

2xCH
2.0 H
CH
0.9 H
NCH
3
+OCH
2

5.1 H
HOD

5xCH
2

10.4 H
NMR
Solvent
CH
2

2.0 H
CH
3

3.1 H
CH
3

3.1 H

Lot Number: BDG 4434
Proton NMR Spectrum oI -DesmethylsildenaIil in DMSO-d
3/

25 25 50 50 75 75 100 100 125 125 150 150 175 175 200 200
2xC
C
C=O
2xCH
CH
3xC
2xCH
3
C
OCH
2

4xNCH
2

NCH
3

CH
2

CH
2

NMR
Solvent

Lot Number: BDG 4434
Carbon-13 NMR Spectrum oI -DesmethylsildenaIil in DMS-d6
45