Reaktion #61690

Reaktionsgleichung

sodium carbonate

7,7a-Dihydro-5-iodo-7-isopropyl-N-methyl-4aH-pyrrolo[2,3-d]pyrimidin-4-amine

dimethoxy ethyleneglycol

3-Hydroxyphenylboronic acid

→

desired product

Ausbeute 74.4%

7,7a-Dihydro-7-isopropyl-N-methyl-5-phenyl-4aH-pyrrolo[2,3-d]pyrimidin-4-amine

Ausbeute 74.4%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigethe vessel was purged with argon
3. 3
   TemperaturThe reaction was subsequently cooled
4. 4
   Filtrationfiltered through a bed of celite
5. 5
   SonstigeThe filtrate was evaporated in vacuo
6. 6
   SonstigeSilica gel chromatography (ethyl acetate:hexanes) and evaporation in vacuo of the requisite fractions

Vorschrift

7,7a-Dihydro-5-iodo-7-isopropyl-N-methyl-4aH-pyrrolo[2,3-d]pyrimidin-4-amine (0.15 g, 0.475 mmol) from above was placed in a 50 ml round bottom flask, whereupon 12 ml dimethoxy ethyleneglycol was added. 3-Hydroxyphenylboronic acid (0.262 g, 1.9 mmol pre-dissolved in 3.3 ml ethanol) was added at once, and was followed by 1.9 ml saturated aqueous sodium carbonate. Pd0(PPh3)4 (55 mg, 47 umol) was added to the reaction, the vessel was purged with argon, and set to stir at 80 C for 48 h. The reaction was subsequently cooled, and filtered through a bed of celite. The filtrate was evaporated in vacuo, and the residual material was adhered to silica gel using ethyl acetate as solvent. Silica gel chromatography (ethyl acetate:hexanes) and evaporation in vacuo of the requisite fractions yielded the desired product (94.8 mg, 70.7% yield). 1H NMR (399.6 MHz, d6-DMSO) δ 1.76 (6H, d, J=6.8 Hz), 5.03 (3H, d, J=4.8 Hz), 5.34 (1H, sp, J=6.4 Hz), 5.53 (1H, q, J=4.8 Hz), 6.73 (1H, m), 6.85 (1H, m), 7.25 (1H, app t, J=7.6 Hz), 7.37 (1H, s), 7.59 (1H, s).

Quelle