1,2-Dichloroethane → HCID 86669204, compound

HRID 69959Notes

Reaction equation

HRID 69959 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]([CH3:14])[N:11]=[C:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=1.[NH2:23][C:24]1[C:25]([C:32](O)=[O:33])=[N:26][C:27]([Br:31])=[C:28]([F:30])[CH:29]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[NH2:23][C:24]1[C:25]([C:32]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH:9]=2)=[O:33])=[N:26][C:27]([Br:31])=[C:28]([F:30])[CH:29]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 69047460Tert-butyl 6-(3-aminopyridin-4-yl)-2-methylpyrimidin-4-ylcarbamateHCID 726988793-Amino-6-bromo-5-fluoropicolinic acid

Product 1

HCID 86669204HCID 86669204, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method 27 was followed using tert-butyl 6-(3-aminopyridin-4-yl)-2-methylpyrimidin-4-ylcarbamate (1.0 equiv.), 3-amino-6-bromo-5-fluoropicolinic acid (1.0 equiv.), EDC (1.0 equiv.), and HOAt (1.0 equiv.) in DMF yielding tert-butyl 6-(3-(3-amino-6-bromo-5-fluoropicolinamido)pyridin-4-yl)-2-methylpyrimidin-4-ylcarbamate in 15% yield. LCMS (m/z): 520.1 (MH+); LC Rt=3.4 min.

Sources & evidence

ORD record
ord-f66a3f1c2adf4a26bfbba464a7c70d65
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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