Réaction #91298

Équation de réaction

Chlorotrimethylsilane

Sodium ({2-[(Methyloxy)carbonyl]-1-cyclopenten-1-yl}amino)acetate

sodium thiocyanate

water

water

→

title compound

Rendement 83.0%

(4-Oxo-2-thioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetic acid

Rendement 83.0%

Solvants

N-methylpyrrolidinone

Conditions de réaction

Traitement

1. 1
   TempératureAfter 3 hours at this temperature the reaction mixture was cooled to 90° C.
2. 2
   TempératureThe mixture was cooled to 2° C.
3. 3
   Autrethe product isolated by filtration
4. 4
   LavageIt was washed with water (2×120 ml)
5. 5
   Séchageacetone (2×60 ml) and dried at 60° C. in an oven under reduced pressure

Mode opératoire

Sodium ({2-[(Methyloxy)carbonyl]-1-cyclopenten-1-yl}amino)acetate (60 g) and sodium thiocyanate (26.6 g) were stirred in N-methylpyrrolidinone (240 ml) and water (2.94 ml) under a nitrogen atmosphere. Chlorotrimethylsilane (73.8 g) was added and the mixture heated to 117±3° C. After 3 hours at this temperature the reaction mixture was cooled to 90° C. and water (480 ml) was added. The mixture was cooled to 2° C. and the product isolated by filtration. It was washed with water (2×120 ml) then acetone (2×60 ml) and dried at 60° C. in an oven under reduced pressure to yield the title compound as an off-white solid (50.69 g, 83%). 1H NMR (d6 DMSO) δ 2.00 (2H, quintet), 2.60 (2H, t), 2.87 (2H, t), 4.95 (2H, broad s), 12.57 (1H, broad s), 13.26 (1H, broad s).

Source