Synthesis
Example 180: Synthesis of N-(1-methyl-1H-pyrazol-4-yl)-1-(2-morpholinobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine Step (i): 2-fluorobenzaldehyde (0.5 mL, 4.8 mmol), morpholine (0.6 mL, 1.5 eq.), and potassium carbonate (1.3 g, 2 eq.) were mixed and heated in a microwave reactor at 125 °C for 2.5 hours. Upon completion of the reaction, the solvent was removed by evaporation. The residue was partitioned between water and dichloromethane (DCM) and the aqueous phase was further extracted with DCM. All organic phases were combined, dried over sodium sulfate and subsequently concentrated under vacuum to give 2-morpholino benzaldehyde (0.57 g, 63% yield).
References
[1] Russian Chemical Bulletin, 2004, vol. 53, # 6, p. 1240 - 1247
[2] Synthesis, 2010, # 24, p. 4287 - 4299
[3] Patent: WO2011/48082, 2011, A1. Location in patent: Page/Page column 160; 161
[4] Medicinal Chemistry Research, 2015, vol. 24, # 9, p. 3516 - 3528
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 1679 - 1682
