5, 2, 7, 4, 1, 8, 3, 6, 9
From clue 4, the sum of the first 4 digits to be pressed, the last 4 digits to be pressed, and two times the 5th digit to be pressed is 19 + 27 = 46. The sum of the first and last 4 digits to be pressed and the 5th digit must be the sum of the digits 1-9, from clue 1. This sum is 45, meaning the 5th digit is 46-45 = 1.
From clues 2 and 3, 2 must be the 2nd digit and 4 must be the 4th digit.
From clue 3, 7 must be the 1st or 3rd digit pressed since it can not be pressed before or after the 6 or 8. From clue 4, this means 5 must be pressed 1st or 3rd. But, from clue 2, it can not be the 3rd digit, so it must be the first, meaning 7 is the 3rd digit pressed.
That leaves 3, 6, 8, and 9 as the last 4 digits to be pressed. If 8 were pressed 8th, then the 9 must be pressed 6th, a contradiction with clue 4. So 8 must be pressed 6th meaning 9 is to be pressed last. This leaves 6 to be entered 8th and 3 to be entered 7th.