HCID 21843640, compound → 1-{2-[4-(7-Bromo-benzo[b]thiophen-2-yl)-5-fluoro-pyrimidin-2-ylamino]-ethyl}-imidazolidin-2-one

HRID 422107Notes

Reaction equation

HRID 422107 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][NH:6][C:5]1=[O:9].[Br:10][C:11]1[C:16]2[S:17][C:18]([C:20]3[C:25]([F:26])=[CH:24][N:23]=[C:22](Cl)[N:21]=3)=[CH:19][C:15]=2[CH:14]=[CH:13][CH:12]=1>O1CCOCC1>[Br:10][C:11]1[C:16]2[S:17][C:18]([C:20]3[C:25]([F:26])=[CH:24][N:23]=[C:22]([NH:1][CH2:2][CH2:3][N:4]4[CH2:8][CH2:7][NH:6][C:5]4=[O:9])[N:21]=3)=[CH:19][C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 21843640HCID 21843640, compoundHCID 86640259HCID 86640259, compound

Product 1

HCID 666735331-{2-[4-(7-Bromo-benzo[b]thiophen-2-yl)-5-fluoro-pyrimidin-2-ylamino]-ethyl}-imidazolidin-2-oneYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine 1-(2-aminoethyl)-2-imidazolone (100 g, 774 mmol) with 4-(7-bromo-benzo[b]thiophen-2-yl)-2-chloro-5-fluoro-pyrimidine (90 g, 262 mmol) in 1,4-dioxane (650 mL) and heat to 90° C. with stirring under nitrogen for 3 hours. Cool the reaction to room temperature. Filter and wash the solid with water (3×500 mL) and diethyl ether (500 mL). Vacuum-dry at 50° C. to give the title compound (59.2 g, 52%) as a yellow solid. MS (ES) m/z 436 [M+1]+.

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. filtrationFilter
  4. washwash the solid with water (3×500 mL) and diethyl ether (500 mL)
  5. customVacuum-dry at 50° C.

Sources & evidence

ORD record
ord-8ff4da10ab7745219b65890936853024
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

Loading…