반응 #335237

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N-methylmorpholine

4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid

1,3-dipropyl-5,6-diaminouracil

isobutyl chloroformate

→

title compound

수율 90.7%

2-[[4-[3-[(6-Amino-1-propyl-1,2,3,4-tetrahydro-3-propyl-2,4-dioxo-5-pyrimidinyl)amino]-2-methyl-3-oxopropyl]phenyl]oxy]-acetic acid, 1,1-dimethylethyl ester

수율 90.7%

용매

ethyl ether

tetrahydrofuran

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGStir for 3 hours at -20° C.
2. 2
   온도warm to room temperature
3. 3
   기타Separate the organic phase
4. 4
   세척wash with water (200 mL)
5. 5
   건조dry (MgSO4)
6. 6
   기타Evaporate the solvent in vacuo
7. 7
   기타purify by flash chromatography (5→10% methanol/chloroform

실험 절차

Dissolve 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid (1.07 g, 3.64 mmol) in tetrahydrofuran (15 mL) and treat with N-methylmorpholine (0.4 mL, 3.64 mmol). Cool to -20° C. and treat with isobutyl chloroformate (0.47 mL, 3.64 mmol). Stir for 30 minutes and add a solution of 1,3-dipropyl-5,6-diaminouracil (0.82 g, 3.64 mmol) in dimethylformamide (5 mL). Stir for 3 hours at -20° C., warm to room temperature and dilute with ethyl ether (200 mL). Separate the organic phase, wash with water (200 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography (5→10% methanol/chloroform then 5→10→20% isopropanol/hexane) to yield the title compound (1.66 g).

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