Methyl iodide → (S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-ylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate methyliodide

HRID 407902Notes

Reaction equation

HRID 407902 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:30])[C@@H:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][CH2:19][S:20][CH3:21])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].[CH3:31][I:32]>>[CH3:31][I:32].[CH2:1]([C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([NH:15][C:16](=[O:30])[C@@H:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:18][CH2:19][S:20][CH3:21])[CH2:13][CH2:14]2)=[N:5][CH:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 67469820(S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-ylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate

Product 1

HCID 86688086(S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-ylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate methyliodideYield 120%

Procedure

A solution of (S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-ylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate (4.4 g, 10 mmol) in neat methyl iodide (22 mL, 340 mmol) stirred at ambient temperature for 18 hours. The reaction was evaporated to dryness to yield (S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-ylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate methyliodide (7 g, 12 mmol, >95%).

Workup

  1. customThe reaction was evaporated to dryness

Sources & evidence

ORD record
ord-e386d2f0073e48ee835c7d1476fcb586
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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