Reaction #677804

Reaction equation

2,6-diamino-4-hydroxypyrimidine

sodium acetate

Methyl 4-(2-bromoacetyl)benzoate

→

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

Solvents

water

MeOH

Conditions

Workup

1. 1
   workup.ADDITIONwas added slowly to the above solution
2. 2
   Temperaturecooled to room temperature
3. 3
   FiltrationThe residue was filtered
4. 4
   Otherdried
5. 5
   workup.STIRRINGIt was then stirred in CH2Cl2 (10 mL)
6. 6
   Filtrationfiltered
7. 7
   Otherto provide XI-8-I (1.07 g, 47.5%)

Procedure

A solution of 2,6-diamino-4-hydroxypyrimidine (CAS: 56-06-4, 1 g, 7.93 mmol) and sodium acetate (0.85 g, 10.32 mmol) in water (180 mL) was stirred at 100° C. for 30 minutes. Methyl 4-(2-bromoacetyl)benzoate (2.24 g, 8.72 mmol) was suspended in MeOH (25 mL) and was added slowly to the above solution. The reaction mixture was then stirred at 100° C. for 16-20 h and then cooled to room temperature. The residue was filtered and dried. It was then stirred in CH2Cl2 (10 mL) and filtered to provide XI-8-I (1.07 g, 47.5%). LCMS: m/z 285 (M+1)+.

Source