Triethylamine → HCID 60204427, compound

HRID 507559Notes

Reaction equation

HRID 507559 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:9][C:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.[NH2:23][CH2:24][CH2:25][N:26]1[C:30]([CH3:32])([CH3:31])[C:29](=[O:33])[NH:28][C:27]1=[O:34].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:31][C:30]1([CH3:32])[N:26]([CH2:25][CH2:24][NH:23][C:2]2[N:7]=[C:6]([C:8]3[S:9][C:10]([S:13]([C:16]4[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=4)(=[O:15])=[O:14])=[CH:11][CH:12]=3)[CH:5]=[CH:4][N:3]=2)[C:27](=[O:34])[NH:28][C:29]1=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 574288041-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dioneHCID 60204428HCID 60204428, compound

Product 1

HCID 60204427HCID 60204427, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-chloro-4-(5-tosylthiophen-2-yl)pyrimidine (100 mg, 0.23 mmol), 1-(2-aminoethyl)-5,5-dimethylimidazolidine-2,4-dione (33 mg, 0.26 mmol) and triethylamine (28 mg, 0.27 mmol) in toluene (3 mL) was heated at 160° C. for 35 min in a Personal Chemistry microwave reactor. Upon cooling to rt the precipitate was filtered and washed with diethyl ether. The solid was put into 2 mL of methanol and the suspension was stirred for about 15 min and filtered to afford the title compound as pale yellow crystals (56 mg, 50%). MS (M+H)+ 486.

Workup

  1. temperatureUpon cooling to rt the precipitate
  2. filtrationwas filtered
  3. washwashed with diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c49ec8e56ba64c33a08d6491a931be26
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

Loading…