N-(2-Aminoethyl)ethyleneurea → HCID 60204554, compound

HRID 2267431Notes

Reaction equation

HRID 2267431 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[C:12]([CH3:13])=[CH:11][N:10]=[C:9](S(C)(=O)=O)[N:8]=2)=[CH:4][CH:3]=1.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][NH:23][C:22]1=[O:26]>C1(C)C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([C:7]2[C:12]([CH3:13])=[CH:11][N:10]=[C:9]([NH:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][NH:23][C:22]3=[O:26])[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80480N-(2-Aminoethyl)ethyleneureaHCID 60204556HCID 60204556, compound

Product 1

HCID 60204554HCID 60204554, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

4-(5-Bromothiophen-2-yl)-5-methyl-2-(methylsulfonyl)pyrimidine (2 g, 6 mmol) in toluene (10 mL) was treated with 1-(2-aminoethyl)imidazolidin-2-one (1.489 g, 10.2 mmol) and the reaction stirred at 120° C. overnight. The volatiles were removed in vacuo and the residue purified by flash chromatography using a gradient of 2 to 10% methanol in dichloromethane to obtain a light yellow solid (1.8 g). MS (M+H)+ 383.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-49eaed8eeff74ad6a32a5a9c00c9401c
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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