Dimethyl Sulfide → 1-(3-Pyridin-2-yl-imidazo[1,2-a]pyrimidin-2-yl)-ethylamine

Reaction equation

C(OC(=O)[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]2[C:21]=1I)[CH3:12])C1C=CC=CC=1.CSC.[C:27](O)([C:29](F)(F)F)=O>>[N:10]1[CH:29]=[CH:27][CH:21]=[CH:13][C:11]=1[C:21]1[N:16]2[CH:17]=[CH:18][CH:19]=[N:20][C:15]2=[N:14][C:13]=1[CH:11]([NH2:10])[CH3:12]

Participants

Reactant 3

HCID 1068Dimethyl Sulfide

HCID 6422Trifluoroacetic acid

HCID 67432510[1-(3-Iodo-imidazo[1,2-a]pyrimidin-2-yl)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 674320071-(3-Pyridin-2-yl-imidazo[1,2-a]pyrimidin-2-yl)-ethylamine

Procedure

A mixture of [1-(3-iodo-imidazo[1,2-a]pyrimidin-2-yl)-ethyl]-carbamic acid benzyl ester (900 mg, 2.4 mmol) and dimethylsulfide (0.9 mL) in TFA (4.5 mL) was stirred at rt overnight. The mixture was concentrated in vacuo, dissolved in EtOAc washed with satd. sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo to provide 1-(3-pyridin-2-yl-imidazo[1,2-a]pyrimidin-2-yl)-ethylamine: LC-MS (ESI) m/z 240.0 [M+H]+.