Reaktion #598796

Reaktionsgleichung

3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanoic acid

N,N-Diisopropylethylamine

4-tert-butylbenzene-1,2-diamine

N,N-Dimethylformamide

→

solid

Ausbeute 42.1%

N-(2-amino-4-(tert-butyl)phen yl)-3-(3-((((3 aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanamide

Ausbeute 42.1%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenpartially concentrated to ca. 2 mls
2. 2
   workup.ADDITIONNaHCO3 (saturated) was added
3. 3
   ExtraktionThe mixture was extracted with EtOAc (3×)
4. 4
   Trocknenthe combined organics were dried with MgSO4
5. 5
   Einengenconcentrated
6. 6
   SonstigePurified by flash chromatography (DCM/7N NH3 in MeOH 95:5)

Vorschrift

N,N,N′,N′-Tetramethyl-0-(7-azabenzotriazol-1-yl}uronium Hexafluorophosphate (0.44 g, 1.2 mmol) added to a solution of 3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanoic acid (460 mg, 0.77 mmol) and N,N-Diisopropylethylamine (0.44 mL, 2.6 mmol) and 4-tert-butylbenzene-1,2-diamine (0.15 g, 0.93 mmol) in N,N-Dimethylformamide (5 mL, 60 mmol). The reaction was stirred overnight at RT, partially concentrated to ca. 2 mls and then NaHCO3 (saturated) was added. The mixture was extracted with EtOAc (3×) and the combined organics were dried with MgSO4 and concentrated. Purified by flash chromatography (DCM/7N NH3 in MeOH 95:5) to yield a solid (0.24 g).

Quelle