It may be difficult to pull off a deal if the Merseyside club remain interested, but Leeds United may not have a better opportunity to try.
Steve Evans has previously claimed that should Leeds United find themselves in a position from which they are only looking up in January - rather than over their shoulder - then owner Massimo Cellino is likely to support him with funds during the winter window (via Yorkshire Evening Post).
And while the Italian will want to invest in a potential charge for a play-off spot, rather than looking too far into the future, Evans would be foolish not to suggest a move for a prospect whose reputation in the game is growing with almost every appearance.
Portsmouth's Conor Chaplin emerged onto the scene last season for the League Two side, having come through the youth ranks at Fratton Park. But it is during this campaign that people are really starting to take notice of the young striker.
The 18-year-old has helped Pompey make an excellent start to the season - Paul Cook's men currently sit fourth in the table, just one point off an automatic promotion spot, and just three behind table-toppers Plymouth. Chaplin has scored five league goals from 14 appearances, including the side's late winner over high-flyers Northampton at the weekend. His tally is all the more impressive given that he has started just four of those 14 games.
Portsmouth's solid start makes January the perfect time for Evans to go after the young forward. Should the south-coast club get promoted, Chaplin's price is likely to rise considerably.
While it is certainly a gamble to go after a striker who has enjoyed just over a year in professional football, and in League Two at that, the gamble will become greater should Leeds wait until Pompey are promoted, as several more teams are likely to be aware of his potential, and thus, his value could rise further.
And while Chaplin is inexperienced, he has shown glimpses of real quality against the sides that Leeds are competing with for a place in the Premier League.
In the Capital One Cup, the starlet scored in the defeat to Reading, having already bagged the winner in the previous round against Derby County.
And it was his goal against the Rams that showed what a special player he could be. He would have been forgiven for getting carried away for smashing his effort over the bar when a 76th minute cross was drilled into his path. However, he showed amazing composure to let the ball run across him slightly, before guiding his strike into the bottom corner to create the kind of atmosphere that Fratton Park may not have experienced since their days in the top flight.
That goal may well have brought him to the attention of several Premier League sides, which will make Leeds' task much more difficult if they try to sign him in January. The News previously reported that Liverpool had sent a scout to watch the youngster when Pompey faced Oxford in September. And the lure of learning under Jurgen Klopp may well be difficult for Chaplin - who signed a new deal earlier in the season that will keep him at Portsmouth (via The News) - to turn down.
However, Leeds potentially have their own secret weapon that could help to convince Chaplin that a move to Elland Road is right for his career, United's current academy director and under-21 manager Paul Hart.
With Chaplin struggling to hold down a first-team place at Fratton Park, and Evans having to regularly leave the likes of Lee Erwin out of his matchday squad, it seems likely that Chaplin's opportunities would initially be restricted to appearances for the U21 squad. Fortunately, he will have some experience of working with Hart.
Hart joined Portsmouth in 2007 as Director of Youth Operations, just a few years after Chaplin joined the club as a six-year-old. While Chaplin's tender age most likely prevented the pair working closely on too many occasions before Hart left in 2009, having an understanding of what he can expect from the coach in charge of his progression may make Thorp Arch a very attractive prospect.
Going after Chaplin may be the kind of gamble that Cellino would prefer to consider in the summer, especially if a promotion push seems possible when the next window opens. But he is undoubtedly a special talent, and thus, needs to be on Leeds' radar in January.