Reacción #519339

ord-51ce83e69ceb4097a9f8caf6ec877b12

Ecuación de reacción

N#Cc1c(N)n[nH]c1-c1ccc(Oc2ccccc2)cc1
3-Amino-4-cyano-5-(4-phenoxyphenyl)pyrazole
O
water
NC=O
formamide
Nc1ncnc2[nH]nc(-c3ccc(Oc4ccccc4)cc3)c12
pure product
Rendimiento 80.0%
Nc1ncnc2[nH]nc(-c3ccc(Oc4ccccc4)cc3)c12
4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine
Rendimiento 80.0%

Condiciones de reacción

Temperatura
180°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONadded
  2. 2
    Otrothe solid collected
  3. 3
    Lavadowashed well with water
  4. 4
    Secadomethanol and dried in air

Procedimiento

3-Amino-4-cyano-5-(4-phenoxyphenyl)pyrazole (Intermediate AB) (29.5 g) was suspended in 300 mL formamide and heated under nitrogen at 180° C. for 4 hours, cooled to 30 C, 300 mL water added and the solid collected, washed well with water then methanol and dried in air giving 24.6 g pure product (80%) of 4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine m.p. 267-269° C. as pale brown-grey solid. Calculated for C17H13N5O C 67.3H 4.3 N 23.1 Found C 67.0H 4.4 N 23.1.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06660744B1uspto-grants-2003_12