Reacción #1704434

ord-9d98d595517e4862b82eace92a89943c

Ecuación de reacción

Cc1nc(N)nc(Cl)c1Cc1ccc(CC#N)cc1
product
Cc1nc(N)nc(Cl)c1Cc1ccc(CC#N)cc1
2-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile
CCC[C@H](N)CCO
(S)-3-aminohexan-1-ol
CCCCO
butan-1-ol
[K+].[OH-]
KOH
CCC[C@@H](CCO)Nc1nc(N)nc(C)c1Cc1ccc(CC(=O)O)cc1
subtitle compound
CCC[C@@H](CCO)Nc1nc(N)nc(C)c1Cc1ccc(CC(=O)O)cc1
(S)-2-(4-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas sealed into a microwave tube
  2. 2
    Otrowas performed in the CEM Microwave, at 160° C.
  3. 3
    TemperaturaThe mixture was cooled
  4. 4
    Otrothe solvent evaporated under reduced pressure
  5. 5
    OtroThe residue was purified by RPHPLC

Procedimiento

A mixture of the product of example 81 step (iii) (0.4 g) and (S)-3-aminohexan-1-ol (0.5 g) in butan-1-ol (3 mL) was sealed into a microwave tube. The reaction was performed in the CEM Microwave, at 160° C. and 100 W for 1.5 h. Aq. 5M KOH (iml) was added and the mixture heated at 100° C. for 48 h. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was purified by RPHPLC to give the subtitle compound, 174 mg.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08765939B2uspto-grants-2014_07