Reacción #1269843

ord-b91a2c85966e4a2ba3dd38e25348a084

Ecuación de reacción

C1CCC2=NCCCN2CC1
DBU
CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F
BOP
Cn1c(=O)cc[nH]c1=O
3-Methyluracil
Cl.N[C@@H]1CCC[C@H]1O
(1R,2R)-(−)-2-hydroxycyclopentylamine hydrochloride salt
Cn1c(N[C@@H]2CCC[C@H]2O)nccc1=O
product
Rendimiento 76.5%
Cn1c(N[C@@H]2CCC[C@H]2O)nccc1=O
2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one
Rendimiento 76.5%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGThe mixture was stirred at room temperature overnight
  2. 2
    OtroThe reaction mixture was purified by a semi-preparative HPLC

Procedimiento

3-Methyluracil (12.6 mg, 0.1 mmol) was dissolved in 0.5 mL of DMF, and then BOP (71 mg, 0.16 mmol) was added. The mixture was stirred at room temperature for two minutes, then (1R,2R)-(−)-2-hydroxycyclopentylamine hydrochloride salt (22 mg, 0.16 mmol) was added, followed by DBU (51 uL, 3.4 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was purified by a semi-preparative HPLC to give pure product (16 mg, yield 76%). MS (ESI) m/z 210.1 [M+H]+.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08664207B2uspto-grants-2014_03