Cesium carbonate → N'-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl)-N-[2-(dimethylamino)ethyl]-N-methylsulfamide

HRID 1959045Notes

Reaction equation

HRID 1959045 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[N:3]=1.[CH3:20][N:21]([CH3:30])[CH2:22][CH2:23][N:24]([CH3:29])[S:25]([NH2:28])(=[O:27])=[O:26].C1(P(C2CCCCC2)C2(C(C)C)CC=CC=C2C2C(C(C)C)=CC(C(C)C)=CC=2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:19][C:13]1[C:14]([F:18])=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][S:10][C:4]1[N:3]=[C:2]([NH:28][S:25]([N:24]([CH2:23][CH2:22][N:21]([CH3:30])[CH3:20])[CH3:29])(=[O:27])=[O:26])[CH:7]=[C:6]([O:8][CH3:9])[N:5]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11286832{[2-(Dimethylamino)ethyl](methyl)sulfamoyl}amineHCID 671608462-Dicyclohexylphosphino-2,4',6'-tri-isopropyl-1,1'-biphenylHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine2×

Product 1

HCID 59558805N'-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl)-N-[2-(dimethylamino)ethyl]-N-methylsulfamide

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared according to the procedure outlined in example 1 step (iv) using a mixture of 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine (the product of example 35 step i) (0.35 g), N-[2-(dimethylamino)ethyl]-N-methylsulfamide (prepared according to procedure outlined in Org. Letts 2004, 6 (16), 2705-2708) (0.18 g), tris(dibenzylideneacetone)dipalladium (0) (73 mg), 2-dicyclohexylphosphino-2,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (53 mg), cesium carbonate (0.39 g) and dioxane (20 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase) then titurated with MeOH followed by Et2O to give the title compound as a white solid. Yield: 0.12 g

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-cef3959651a24d639aba4fa4e196e702
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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