Di-tert-butyl dicarbonate → 4-Chloro-6-ethyl-n,n-di-boc-pyridin-2-amine

HRID 69973Notes

Reaction equation

HRID 69973 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([NH2:10])[CH:3]=1.[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])[CH:3]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 690433694-Chloro-6-ethylpyridin-2-amine

Product 1

HCID 690431084-Chloro-6-ethyl-n,n-di-boc-pyridin-2-amineYield 27%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Method 24 was followed using 4-chloro-6-ethylpyridin-2-amine (1.0 equiv.), BOC2O (2.0 equiv.), and DMAP (cat.) in DCM to yield 4-chloro-6-ethyl-N,N-di-BOC-pyridin-2-amine (27% yield). LCMS (m/z): 357.1 (MH+); LC Rt=4.11 min.

Sources & evidence

ORD record
ord-7d55508c5c474540993a2048df4861e7
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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