Réaction #50298

Équation de réaction

2,4-diamino-6-hydroxypyrimidine

sodium acetate

bromoacetaldehyde diethylacetal

HCl

sodium acetate

→

2-amino-4 -hydroxy-7H-pyrrolo[2,3-d]pyrimidine

Rendement 79.0%

Solvants

water

water

Conditions de réaction

Traitement

1. 1
   Autrewas obtained
2. 2
   TempératureThe solution was cooled to ambient temperature
3. 3
   workup.ADDITIONThe resulting solution was added
4. 4
   Températurehad been heated to 70°-85° C
5. 5
   workup.WAITto proceed for 2 hours at 70°-85° C., at which time
6. 6
   TempératureThe mixture was cooled to 0° C.
7. 7
   workup.STIRRINGstirred for about 1.5 hours
8. 8
   FiltrationThe mixture was then filtered
9. 9
   Lavagethe collected product was washed with 500 mL of water and 500 mL of acetone
10. 10
    Autredried

Mode opératoire

A mixture of 136.7 g of bromoacetaldehyde diethylacetal, 347 mL of water, and 17.3 mL of concentrated HCl was heated to about 90° C. with vigorous stirring for about 30 minutes, at which time a clear solution was obtained. The solution was cooled to ambient temperature and 68.3 g of sodium acetate was added. The resulting solution was added, with stirring, to a suspension of 100 g of 2,4-diamino-6-hydroxypyrimidine and 34.2 g of sodium acetate in 739 mL of water, which had been heated to 70°-85° C. The reaction was allowed to proceed for 2 hours at 70°-85° C., at which time the reaction was complete. The mixture was cooled to 0° C. and stirred for about 1.5 hours. The mixture was then filtered and the collected product was washed with 500 mL of water and 500 mL of acetone, and dried, affording 72.3 g (79%) of 2-amino-4 -hydroxy-7H-pyrrolo[2,3-d]pyrimidine, mp>300° C. NMR δ6.03 (s, 2H), 6.13 (m, 1H), 6.56 (dd, J=3.3, 2.3 Hz, 1H), 10.23 (br s, 1H), 10.93 (br s, 1H).

Source