But Fenway Sports Group, the club's American owners, said he would not go

Philippe Coutinho does not want to play for Liverpool again after he stunned them on the eve of the new season with a transfer request.

The Brazil international, who has been the subject of two failed bids from Barcelona, sent an email to Liverpool's Sporting Director Michael Edwards Friday lunchtime informing him of his wish to quit the club. It was immediately rejected.

Coutinho's demand came on a dramatic day for Liverpool, which started with Fenway Sports Group, the club's American owners, issuing a statement to say they would not sanction the 25-year-old's sale at any price and considered the matter closed.

Philippe Coutinho's transfer request rocked Liverpool and 'lost the trust' of boss Jurgen Klopp

Liverpool have already rejected two transfer offers from Barcelona for the Brazilian star

The playmaker has a fractured relationship with Klopp, according to Coutinho's family member

Jurgen Klopp then followed up in his press conference by relaying a similar message and he left the Press auditorium at Melwood, Liverpool's training ground, before midday thinking a line had been drawn under the issue.

However, things took an unexpected twist when Sky Sports reported that Coutinho – who is out of Saturday's game at Watford and won't figure in Tuesday's Champions League play-off in Hoffenheim due to a back injury – had made a move to engineer his departure.

This development is something Liverpool have dreaded all summer and the timing, ahead of two games of huge importance, could not be worse for the club. Coutinho, for his part, had not wanted to take this drastic action either but now he feels he has no choice.

As far as he is concerned, though, a line has been drawn and a close family member was quoted as saying: 'Philippe has tried very hard to find an amicable solution to this situation but to no avail. He has tremendous love for the club and its fans.

FSG, the club's owners, said Coutinho would not leave and Klopp relayed a similar message

'But like Steven Gerrard and Luis Suarez have pointed out in the past, Liverpool does not let its players leave on amicable terms.'

More worryingly for Liverpool, the family member explained that his relationship with Klopp has fractured, saying that he 'does not have the trust of his manager'.

The family member added: 'There are things that have happened, there is not the same bond. It is regretful, but that is the case. There is no going back.'

It is now clear the next 20 days will be fraught and Barcelona will be encouraged to return, perhaps even offering a player as well as cash, after bids of £72million and £90million were rebuffed. Coutinho has his heart set on a move to the Nou Camp and that fact has not been lost within Liverpool's dressing room.

Coutinho had not wanted to take this drastic action either but now he feels he has no choice

There is a belief that the Liverpool top brass will not buckle and cave in to Coutinho's demands

Yet, by the same token, there is also a belief within the group that Liverpool will not buckle and cave in to Coutinho, who has been forcefully reminded of his requirement to maintain professional standards at all times and not let his discipline slip.

In the last eight years, Liverpool have seen a succession of top players be lured away – Xabi Alonso, Javier Mascherano, Fernando Torres, Luis Suarez and Raheem Sterling – and they cannot afford to lose this battle, which was emphasised by the tone of FSG's statement.

It read: 'We wish to offer clarity as regards our position on a possible transfer of Philippe Coutinho. The club's definitive stance is that no offers for Philippe will be considered and he will remain a member of Liverpool Football Club when the summer window closes.'

Klopp believes Liverpool would not be able to buy a suitable replacement if Coutinho left

The message from Anfield has been consistent throughout and even if they were to receive a huge windfall, they would not be able to recruit a comparable replacement. It was a subject Klopp alluded to before learning that Coutinho had submitted his request.

'I had to sell a lot of players in my managerial career,' said Klopp, who said his own pursuit of players will run until August 31. 'Some had clauses, some had no clauses. The only thing I can say about this is that in life everything is about timing – whichever club asks early enough.

'But you cannot come up, close to the start of the season and things like this. It's like I said: the club is bigger than anybody. That is the most important thing. It's about doing it in the right moment. It's how we try do it when we want to bring players in.

'That is how it is. It is about timing. That is how I understand. And that is all I have to say. Maybe everybody has a price – in the right moment. In the wrong moment? No price. Everything is not like it should be but it is a normal situation.