Potassium Carbonate → HCID 89442416, compound

HRID 632730Notes

Reaction equation

HRID 632730 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.Cl.Cl.[NH2:12][C:13]1([CH2:18][NH:19][C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[CH2:17][CH2:16][NH:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[NH2:12][C:13]1([CH2:18][NH:19][C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[CH2:17][CH2:16][N:15]([C:7]2[C:2]([Br:1])=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 89442626HCID 89442626, compound

Product 1

HCID 89442416HCID 89442416, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-6-chloropyrimidin-4-amine (272.7 mg; 1.24 mmol; 1.02 eq.), N-[(3-aminopyrrolidin-3-yl)-methyl]-2,4-difluorobenzamide dihydrochloride (400.0 mg; 1.22 mmol; 1.0 eq.), potassium carbonate (336.8 mg; 2.44 mmol; 2.0 eq.) in DMSO (5.00 ml) was stirred at 60° C. overnight. The reaction mixture was workup and the crude was purified by reverse phase pre-HPLC (Waters, basic condition) to afford the title compound in 76% yield. LC-MS: (M+1=427, obsd.=427).

Workup

  1. customthe crude was purified by reverse phase pre-HPLC (Waters, basic condition)

Sources & evidence

ORD record
ord-e30c2b8105f34beeb43fc14fd7dd21a1
Source dataset
uspto-grants-2016_04
Patent number
US09321760B2

Reaction notes

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