Reaction #939042

Reaction equation

acetic

4,5-Diamino-6-hydroxypyrimidine

sodium hydrogen carbonate

4-isobutoxy-3-nitrobenzoyl chloride

hydrochloric acid

→

desired compound

Yield 69.0%

4-Amino-6-hydroxy-5-(4-isobutoxy-3-nitrobenzoyl)aminopyridine

Yield 69.0%

Solvents

water

ethyl acetate

Conditions

Workup

1. 1
   Temperatureunder cooling with ice
2. 2
   Temperatureunder cooling with ice
3. 3
   Otherplaced under reduced pressure at room temperature
4. 4
   workup.DISTILLATIONto distill ethyl acetate off, and
5. 5
   workup.STIRRINGstirred for 30 min. at room temperature
6. 6
   FiltrationThe precipitated solid product was collected by filtration
7. 7
   Washwashed successively with water and diethyl ether
8. 8
   Otherdried successively in air and reduced pressure

Procedure

4,5-Diamino-6-hydroxypyrimidine (527 mg, 4.18 mmol) was added to an aqueous suspension of sodium hydrogen carbonate (3.15 g, 41.8 mmol) in water (10 mL) under cooling with ice. Subsequently, a solution of 4-isobutoxy-3-nitrobenzoyl chloride (1.08 g, 4.18 mmol) in ethyl acetate (10 mL) was added. The resulting mixture was stirred for 3 hours under cooling with ice, made acetic by addition of 6 M hydrochloric acid, placed under reduced pressure at room temperature to distill ethyl acetate off, and stirred for 30 min. at room temperature. The precipitated solid product was collected by filtration, washed successively with water and diethyl ether, and dried successively in air and reduced pressure, to give 963 mg (yield 69%) of the desired compound in the form of a powdery product.

Source