Ethyl 2-isocyanatopropionate → 5-Methyl-3-(2-(4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidine-2,4-dione

HRID 2267335Notes

Reaction equation

HRID 2267335 reaction equation
[N:1]([CH:4]([CH3:10])[C:5]([O:7]CC)=O)=[C:2]=[O:3].[NH2:11][CH2:12][CH2:13][NH:14][C:15]1[N:20]=[C:19]([C:21]2[S:22][C:23]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[CH:24][CH:25]=2)[CH:18]=[CH:17][N:16]=1>ClCCl>[CH3:10][CH:4]1[NH:1][C:2](=[O:3])[N:11]([CH2:12][CH2:13][NH:14][C:15]2[N:20]=[C:19]([C:21]3[S:22][C:23]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[CH:24][CH:25]=3)[CH:18]=[CH:17][N:16]=2)[C:5]1=[O:7]

Participants

4

Reactant 2

HCID 550681Ethyl 2-isocyanatopropionateHCID 60204267N-(2-aminoethyl)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-amine

Product 1

HCID 602044425-Methyl-3-(2-(4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidine-2,4-dioneYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-isocyanatopropanoate (104 mg, 0.73 mmol) was added to a suspension of N-(2-aminoethyl)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-amine (200 mg, 0.66 mmol) in dichloromethane (10 mL) at rt and stirred for 8 h. The solid was filtered off and added to 15 mL of hydrochloric acid (5 M). After refluxing for 6 h, the mixture was cooled to rt and the precipitate was filtered off, washed with water and then dissolved in 10 mL of methanol. 50 mg of potassium carbonate was added and the mixture was stirred for 10 min. 20 mL of dichloromethane was added and the mixture was filtered through Celite. The filtrate was concentrated to give the title compound (180 mg, 68%). MS (M+H)+ 400.

Workup

  1. filtrationThe solid was filtered off
  2. additionadded to 15 mL of hydrochloric acid (5 M)
  3. temperatureAfter refluxing for 6 h
  4. filtrationthe precipitate was filtered off
  5. washwashed with water
  6. dissolutiondissolved in 10 mL of methanol
  7. addition50 mg of potassium carbonate was added
  8. stirringthe mixture was stirred for 10 min
  9. addition20 mL of dichloromethane was added
  10. filtrationthe mixture was filtered through Celite
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0a87ccef0a014c5a8e364936fe8bb6ae
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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