Reaction #1269843

Reaction equation

DBU

BOP

3-Methyluracil

(1R,2R)-(−)-2-hydroxycyclopentylamine hydrochloride salt

→

product

Yield 76.5%

2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

Yield 76.5%

Solvents

DMF

Conditions

Workup

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

Procedure

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]+.

Source