Reaction #677805

Reaction equation

4-(2-bromoacetyl)benzonitrile

2,6-diaminopyrimidin-4-ol

NaOAc

→

title compound

4-(2-amino-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzonitrile

Solvents

MeOH

water

Conditions

Workup

1. 1
   workup.ADDITIONTo this was added
2. 2
   Temperatureheated overnight at 100° C
3. 3
   OtherAfter completion of reaction
4. 4
   Temperaturethe reaction mixture was cooled to 0° C
5. 5
   FiltrationResultant solid product was filtered off
6. 6
   Otherdried under reduced pressure

Procedure

A mixture of 2,6-diaminopyrimidin-4-ol (1 g, 7.93 mmol) and NaOAc (0.846 g, 10.31 mmol) in water (180 mL) was heated to 100° C. for 20 minutes. To this was added a suspension of 4-(2-bromoacetyl)benzonitrile (2.2 gm, 8.73 mmol) [prepared according to procedure mentioned in J. Med. Chem., 2011, 54(12), 4042-4056] in MeOH (25 mL) and heated overnight at 100° C. After completion of reaction, the reaction mixture was cooled to 0° C. Resultant solid product was filtered off and dried under reduced pressure to provide title compound XI-10-I (1.2 g, 100%). LCMS: m/z 252 (M+1)+.

Source