1,2-Dichloroethane → HCID 86669202, compound

HRID 69957Notes

Reaction equation

HRID 69957 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]([S:14][CH3:15])[N:11]=[C:10]([N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=1.[NH2:31][C:32]1[C:33]([C:39](O)=[O:40])=[N:34][C:35]([Br:38])=[CH:36][CH:37]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[NH2:31][C:32]1[C:33]([C:39]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]2[CH:9]=[C:10]([N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[N:11]=[C:12]([S:14][CH3:15])[N:13]=2)=[O:40])=[N:34][C:35]([Br:38])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 454804523-Amino-6-bromopicolinic acidHCID 690443816-(3-aminopyridin-4-yl)-N,N-di-BOC-2-(methylthio)pyrimidin-4-amine

Product 1

HCID 86669202HCID 86669202, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method 27 was followed using 6-(3-aminopyridin-4-yl)-N,N-di-BOC-2-(methylthio)pyrimidin-4-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-(6-(di-BOC-amino)-2-(methylthio)pyrimidin-4-yl)pyridin-3-yl)picolinamide in 30% yield. LCMS (m/z): 632.1/634.0 (MH+); LC Rt=4.55 min.

Sources & evidence

ORD record
ord-c17ceef0800c4941b5fd6acfc16fbf6d
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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