Browse Prior Art Database

4-(6-oxo-1,6-dihydropyrimidin-2-ylamino)benzonitrile

IP.com Disclosure Number: IPCOM000204401D
Publication Date: 2011-Feb-23
Document File: 2 page(s) / 27K

Publishing Venue

The IP.com Prior Art Database

This text was extracted from a PDF file.
This is the abbreviated version, containing approximately 83% of the total text.

Page 01 of 2

4-(6-oxo-1,6-dihydropyrimidin-2-ylamino)benzonitrile

4-(6-oxo-1,6-dihydropyrimidin-2-ylamino)benzonitrile is an intermediate in the process for preparing 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile, which is a new drug, developed by Tibotec, for the treatment of HIV infection.

Provided is a process for the preparation of a crystalline 4-(6-oxo-1,6-dihydropyrimidin-2- ylamino)benzonitrile (HPAB):

H2N

O SMe

H

N

diglyme, reflux H

N

O

H

N

+

N

CN

N

CN

ABN (IM5)

MTHP (IM6)

HPAB

2-methylthio-4-hydroxypyrimidine (15.0 g, 105.5 mmol), p-aminobenzonitrile (14.96 g, 126.6 mmol,
1.2 eq) and bis(methoxyethylether) (30 mL, 2V) were mixed and heated to 167°C. Stirring was continued at the same temperature over night. The resulting slurry was cooled to room temperature, diethylether (20V) was added and stirring was continued for another 0.5h before the mixture was filtered and the filter cake was washed diethyl ether (300 mL, 20V) and water (300 mL, 20V). The resulting light brown solid was recrystallised from DMF (2 mL, 4V) at reflux to give the title compound (7.2 g, 32% yield) polymorphic form I .


Page 02 of 2

2000

a

g

e

:

.

0

0

0

0

.00

0

C

o

t

.

Sca

at

e

:

3

.

0

0

0

[

/

]

o .

S

c

a

e

U t

:

[

d

e

g

]

1600

1200

800

400

0

6.0 10.0 14.0 18.0 22.0 26.0 30.0 34.0 38.0

Main XRD peaks of Form I of 4-(6-oxo-1,6-dihydropyrimidin-2-ylamino)benzonitrileare: 5.3, 7.9,
10.7, 11.4, 13.3, 15.0, 16.1, 17.0, 18.2, 18.6, 22.3, 22.9, 24.2, 25.3 and...

Processing...
Loading...