Reacción #93937

ord-678d938fe117450c94947b855d5556e4

Ecuación de reacción

CNC(=O)NC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O
4
CNC(=O)NC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O
5'-(3-Methylureido)-5'-deoxythymidine
O=N[O-].[Na+]
sodium nitrite
→
Cc1cn([C@H]2C[C@H](O)[C@@H](CNC(=O)N(C)N=O)O2)c(=O)[nH]c1=O
white fine needles
Rendimiento 70.2%
Cc1cn([C@H]2C[C@H](O)[C@@H](CNC(=O)N(C)N=O)O2)c(=O)[nH]c1=O
5'-(3-Methyl-3-nitrosoureido)-5'-deoxythymidine
Rendimiento 70.2%

Reactantes

CNC(=O)NC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O
4
CNC(=O)NC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O
5'-(3-Methylureido)-5'-deoxythymidine
O=N[O-].[Na+]
sodium nitrite

Reactivos

Ninguno

Disolventes

CC(=O)O
acetic acid

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas kept at 0°
  2. 2
    Otroto precipitate out
  3. 3
    FiltraciónThe product was collected by filtration
  4. 4
    Lavadowashed with water
  5. 5
    Temperaturacooled methanol, ether
  6. 6
    Otrodried
  7. 7
    ConcentraciónThe filtrate was concentrated
  8. 8
    Otroan additional fraction of crystals was obtained
  9. 9
    OtroThe combined product was recrystallized from methanol

Procedimiento

To a solution of 4 (1.00 g, 3.35 mmol) in 50% aqueous acetic acid at 0°, sodium nitrite (0.31 g, 4.55 mmol) was added slowly. The reaction mixture was kept at 0° with stirring for 3 h, during which time crystals started to precipitate out. The product was collected by filtration, washed with water, cooled methanol, ether, and dried. The filtrate was concentrated and an additional fraction of crystals was obtained. The combined product was recrystallized from methanol to yield 0.77 g (70%) of white fine needles: mp 159°-160° dec.: uvλmaxEtOH 264 nm (ε11,000); uvλminEtOH 235 nm. Anal. (C12H17N5O6) C, H, N.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04128639uspto-grants-1978_12