Hi and welcome to the HUBB Nukaga san.
I'm afraid I have to say that it is basically impossible.
The furthest east you can get by a normal road is Omsukchan. In winter, there are winter roads further east, they leave the Kolyma Highway somewhere near Ust-Nera, but to go up to Chersky and further east into Chukotka requires expedition-type specialised vehicles. These are not normal winter roads which are graded for standard 4x4s.
You could take a bike to Chukotka by air or boat in summer, but you can't get close to Naukan.
The problem is the terrain - much of it is swamp. In summer it is totally impassable, in winter it is forzen hard, but you can't get any normal vehicle across it. It's also a very tough area due to very heavy snowfall and unpredicatable weather.
Dimitri Kieffer walked across the area with a sled over two winters - have a look at this amazing YT video: https://www.youtube.com/watch?v=N4HQFIJcMDQ.
Please ask if you are interested in other ice roads in Russia - I have spent a lot of time researching them and driving on them.
Best wishes
EO
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EurasiaOverland a memoir of one quarter of a million kilometres by road through all of the Former USSR, Western and Southern Asia.
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