Sodium Iodide → Tert-butyl 5-(morpholinomethyl)pyridin-2-ylcarbamate

HRID 85159Notes

Reaction equation

CS(O[CH2:6][C:7]1[CH:8]=[N:9][C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:11][CH:12]=1)(=O)=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C.O>[O:24]1[CH2:25][CH2:26][N:21]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:9][CH:8]=2)[CH2:22][CH2:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture containing (6-(tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonate (102; 1.21 g, 5.0 mmol), morpholine (48; 1.31 g, 15.0 mmol), K2CO3 (2.10 g, 15.0 mmol) and NaI (0.12 g, 0.75 mmol) in DMF (30 mL) was stirred at 80° C. for 4 h. Upon cooling to room temperature, water (30 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1 to 1:1) to afford tert-butyl 5-(morpholinomethyl)pyridin-2-ylcarbamate 107 (1.40 g, 95%).

Workup

temperatureUpon cooling to room temperature
extractionthe mixture was extracted with ethyl acetate (3×30 mL)
dry with materialThe combined organic layers were dried (MgSO4)
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1 to 1:1)

Sources & evidence

ORD record: ord-3e83d61abc3c48d6a9109a2ced4b43ad
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846947B2

Reaction notes

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