1,2-Dichloroethane → HCID 86669201, compound

HRID 69956

Reaction equation

HRID 69956 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]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=1.[NH2:26][C:27]1[C:28]([C:34](O)=[O:35])=[N:29][C:30]([Br:33])=[CH:31][CH:32]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[NH2:26][C:27]1[C:28]([C:34]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]2[N:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[N:11]=[C:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH:9]=2)=[O:35])=[N:29][C:30]([Br:33])=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 454804523-Amino-6-bromopicolinic acidHCID 69047673Tert-butyl 6-(3-aminopyridin-4-yl)-2-(trifluoromethyl)pyrimidin-4-ylcarbamate

Product 1

HCID 86669201HCID 86669201, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of tert-butyl 6-(3-aminopyridin-4-yl)-2-(trifluoro-methyl)pyrimidin-4-ylcarbamate (1.0 equiv.), 3-amino-6-bromopicolinic acid (1.0 equiv.), HOAt (1.0 equiv.), and EDC (1.0 equiv.) in DMF at a concentration of (0.2 M) was stirred for 3 hrs then heated to 50° C. overnight (homogeneous solution). Water was added to the reaction and the precipitate was filtered. The solid was further purified via SiO2 column chromatography eluting with DCM/MeOH (10%) to yield a brown solid as the desired product (81%). LCMS (m/z): 554.1/556.1 (MH+); LC Rt=3.77 min.

Workup

  1. filtrationthe precipitate was filtered
  2. customThe solid was further purified via SiO2 column chromatography
  3. washeluting with DCM/MeOH (10%)

Sources & evidence

ORD record
ord-d2aa46996bb04bed9468f82fb3d01a4a
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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