Sec Form 4 Filing - Wijngaard Peter @ MEDICINES CO /DE - 2019-12-27

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Wijngaard Peter 2. Issuer Name and Ticker or Trading Symbol MEDICINES CO /DE [ MDCO] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) Chief Development Officer (Last) (First) (Middle) C/O THE MEDICINES COMPANY, 8 SYLVAN WAY 3. Date of Earliest Transaction (MM/DD/YY) 12/27/2019 (Street) PARSIPPANY, NJ07054 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock 12/27/2019 M( 1 ) 50,189 A $ 52.7 52,637 D Common Stock 12/27/2019 M( 1 ) 18,000 A $ 33.27 70,637 D Common Stock 12/27/2019 M( 1 ) 26,250 A $ 29.01 96,887 D Common Stock 12/27/2019 M( 1 ) 35,000 A $ 29.01 131,887 D Common Stock 12/27/2019 M( 1 ) 70,000 A $ 29.01 201,887 D Common Stock 12/27/2019 M( 1 ) 5,000 A $ 29.01 206,887 D Common Stock 12/27/2019 M( 1 ) 125,000 A $ 25.41 331,887 D Common Stock 12/27/2019 F( 2 ) 224,341 D $ 84.78 107,546 D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Stock Option $ 52.7 12/27/2019 M( 1 ) 50,189 ( 3 ) 02/28/2027 Common Stock 50,189 $ 0 0 D Stock Option $ 33.27 12/27/2019 M( 1 ) 18,000 ( 4 ) 02/29/2028 Common Stock 18,000 $ 0 0 D Stock Option $ 29.01 12/27/2019 M( 1 ) 26,250 ( 5 ) 04/23/2028 Common Stock 26,250 $ 0 0 D Stock Option $ 29.01 12/27/2019 M( 1 ) 35,000 ( 6 ) 04/23/2028 Common Stock 35,000 $ 0 0 D Stock Option $ 29.01 12/27/2019 M( 1 ) 70,000 ( 7 ) 04/23/2028 Common Stock 70,000 $ 0 0 D Stock Option $ 29.01 12/27/2019 M( 1 ) 5,000 ( 8 ) 04/23/2028 Common Stock 5,000 $ 0 30,000 D Stock Option $ 25.41 12/27/2019 M( 1 ) 125,000 ( 9 ) 02/28/2029 Common Stock 125,000 $ 0 0 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Wijngaard Peter C/O THE MEDICINES COMPANY 8 SYLVAN WAY PARSIPPANY, NJ07054 Chief Development Officer Signat ures /s/ Stephen M. Rodin, Attorney-in-Fact for Peter Wijngaard 12/31/2019 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Shares of common stock (the "Shares") acquired upon the exercise of options ("Options"). While the Reporting Person has not entered into any agreement requiring that the Reporting Person tender the Shares, the Reporting Person intends to tender or cause to be tendered the acquired Shares pursuant to the tender offer by Medusa Merger Corporation, a Delaware corporation and an indirect wholly owned subsidiary of Novartis AG, to purchase, subject to certain conditions, any and all of the outstanding Shares at a price of $85.00 per Share, net to the seller in cash, without interest thereon and subject to any tax withholding, upon the terms and subject to the conditions set forth in the Offer to Purchase, dated December 5, 2019. ( 2 )Represents shares of common stock withheld for payment of the exercise price and taxes incurred in connection with the exercise of stock options in respect of 329,439 shares. No shares were sold on the market and no cash was received. ( 3 )The option vests in forty-eight equal monthly installments beginning April 1, 2017. On December 27, 2019, the Registrant approved an acceleration of the vesting of 15,684 Shares subject to the option. ( 4 )The option vests in forty-eight equal monthly installments beginning April 1, 2018. On December 27, 2019, the Registrant approved an acceleration of the vesting of 10,125 Shares subject to the option. ( 5 )This performance option becomes exercisable upon the Registrant's achievement of a key company performance goal during a three year period. On December 27, 2019, the Registrant approved an acceleration of the vesting of 26,250 Shares subject to the performance option. ( 6 )This performance option becomes exercisable upon the Registrant's achievement of a key company performance goal during a three year period. On December 27, 2019, the Registrant approved an acceleration of the vesting of 35,000 Shares subject to the performance option. ( 7 )This performance option becomes exercisable upon the Registrant's achievement of a key company performance goal during a three year period. On December 27, 2019, the Registrant approved an acceleration of the vesting of 70,000 Shares subject to the performance option. ( 8 )The performance option, representing a right to purchase a total of 35,000 Shares, becomes exercisable upon the Registrant's achievement of a key company performance goal during a three year period. On December 27, 2019, the Registrant approved a partial acceleration of the vesting of 5,000 Shares subject to the performance option. ( 9 )The option vests in forty-eight equal monthly installments beginning April 1, 2019. On December 27, 2019, the Registrant approved an acceleration of the vesting of 101,562 Shares subject to the option.

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