I have {6-[2-(benzylamino)ethyl]-1,4-dihydropyrimidin-4-yl}methanol (at the top) and have to make the retrosynthesis steps for my class.

I tried different things but I'm not sure about it. In 1 you see I broke off a C-C bond (I know that is difficult to break, do you think it is possible?) Otherwise in 2 is the most obvious way to break but then I would have to make double bonds in the aromatic ring which is also quite difficult. So you see my problem, do you have any ideas?

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  • 2
    $\begingroup$ I mean, those double bonds are still gonna be there even if you manage to find a C–C bond formation reaction in your first choice. $\endgroup$
    – orthocresol
    Dec 3 '21 at 11:54
  • $\begingroup$ @orthocresol yeah but then breaking a C-C bond is not favorable in physiological conditions right? $\endgroup$
    – vupodd
    Dec 3 '21 at 12:17
  • $\begingroup$ Why do physiological conditions matter? Is the synthesis supposed to be done in a human body? I would have assumed you were doing this in the lab. $\endgroup$
    – orthocresol
    Dec 3 '21 at 14:05
  • $\begingroup$ Also, breaking a C–C bond isn't an issue here at all; "breaking" a bond in the retrosynthesis corresponds to the formation of a C–C bond in the forward synthesis. Making C–C bonds is not easy, but not impossible either. My original point, though, was that even if you make that disconnection, you can't avoid the issue of how to make that ring. You might want to think more about that part of it, because it seems like the key to your entire problem. $\endgroup$
    – orthocresol
    Dec 3 '21 at 14:32
  • $\begingroup$ Reductive amination is the best way to install the benzyl group. Consider using an alkyl nitrile as the source of the amine sidechain. $\endgroup$
    – Waylander
    Dec 3 '21 at 14:49

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