1,2-Dichloroethane → 3-amino-6-bromo-N-(4-(2-(di-BOC-amino)-6-methylpyrimidin-4-yl)pyridin-3-yl)picolinamide

HRID 69958Notes

Reaction equation

HRID 69958 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[N:9]=1.[NH2:30][C:31]1[C:32]([C:38](O)=[O:39])=[N:33][C:34]([Br:37])=[CH:35][CH:36]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[NH2:30][C:31]1[C:32]([C:38]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[N:9]=2)=[O:39])=[N:33][C:34]([Br:37])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 454804523-Amino-6-bromopicolinic acidHCID 69047258HCID 69047258, compound

Product 1

HCID 866692033-amino-6-bromo-N-(4-(2-(di-BOC-amino)-6-methylpyrimidin-4-yl)pyridin-3-yl)picolinamideYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method 27 was followed using 4-(3-aminopyridin-4-yl)-N,N-di-BOC-6-methylpyrimidin-2-amine (1.0 equiv.), 3-amino-6-bromopicolinic acid (1.0 equiv), EDC (1.0 equiv.), and HOAt (1.0 equiv.) in DMF yielding 3-amino-6-bromo-N-(4-(2-(di-BOC-amino)-6-methylpyrimidin-4-yl)pyridin-3-yl)picolinamide in 12% yield. LCMS (m/z): 602.2 (MH+); LC Rt=3.60 min.

Sources & evidence

ORD record
ord-96d1e4fb1e8d4ab29237b855cbf960b3
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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