Reaktion #1269843

ord-b91a2c85966e4a2ba3dd38e25348a084

Reaktionsgleichung

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
Ausbeute 76.5%
Cn1c(N[C@@H]2CCC[C@H]2O)nccc1=O
2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one
Ausbeute 76.5%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08664207B2uspto-grants-2014_03