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

HRID 2036640Notes

Reaction equation

HRID 2036640 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

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 6422Trifluoroacetic acidHCID 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]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washwashed with satd
  4. dry with materialsodium bicarbonate solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7641276895a402f989d2f5a424852ce
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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