反应详情

温度

25 °C

N4-{[Trans-4-(3-aminoazetidin-1-yl)cyclohexyl]methyl}-5-nitro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine (20 mg, 0.04 mmol) was dissolved in THF (1.0 mL). To this solution was added benzoic acid (7.3 mg, 0.06 mmol), Polystyrene-linked Carbodiimide (PS-CDI) (47 mg, 0.06 mmol) followed by triethylamine (0.084 mL, 0.06 mmol). The reaction was allowed to stir at 25° C. for 18 h. The reaction was filtered to remove the PS-CDI and the volatiles were removed in vacuo. The crude was redissolved in CH2Cl2 and extracted with 10% aqueous NaHCO3. The aqueous phase was separated and extracted two more times with CH2Cl2. The organic layers were combined, dried (Na2SO4), decanted and concentrated. The resultant residue was purified via flash chromatography (SiO2, 10-30% (2:18:80, NH4OH:CH3OH:CH2Cl2)—CH2Cl2) to afford 18 mg (74%) of the target compound, m/z 600.34 (M+1)+.

1. filtrationThe reaction was filtered
2. customto remove the PS-CDI
3. customthe volatiles were removed in vacuo
4. dissolutionThe crude was redissolved in CH2Cl2
5. extractionextracted with 10% aqueous NaHCO3
6. customThe aqueous phase was separated
7. extractionextracted two more times with CH2Cl2
8. dry with materialdried (Na2SO4)
9. customdecanted
10. concentrationconcentrated
11. customThe resultant residue was purified via flash chromatography (SiO2, 10-30% (2:18:80, NH4OH:CH3OH:CH2Cl2)—CH2Cl2)