N-(2-Aminoethyl)ethyleneurea → 1-(2-(4-(5-Bromothiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

HRID 2267296Notes

Reaction equation

HRID 2267296 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9](Cl)[N:8]=2)=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][NH:19][C:18]1=[O:22]>C(O)(C)C>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][NH:19][C:18]3=[O:22])[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80480N-(2-Aminoethyl)ethyleneureaHCID 15141655HCID 15141655, compound

Product 1

HCID 602042681-(2-(4-(5-Bromothiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-oneYield 68%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(5-bromothiophen-2-yl)-2-chloropyrimidine (1.0 g, 3.63 mmol), 1-(2-aminoethyl)imidazolidin-2-one (0.47 g, 3.63 mmol) and triethylame (0.44 g, 4.36 mmol) in isopropanol (25 mL) was refluxed for 30 h. After cooling down to rt the precipitate was filtered and washed with methanol (5 mL) and dried to give the title compound as a yellow solid (0.9 g, 68%). MS (M+H)+ 368/370.

Workup

  1. temperaturewas refluxed for 30 h
  2. filtrationwas filtered
  3. washwashed with methanol (5 mL)
  4. customdried

Sources & evidence

ORD record
ord-49bf331083b34997903778e5dd69cc07
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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