Sodium Carbonate → 4,6-Bis(4-fluorophenyl)pyrimidin-2-amine

HRID 1161675Notes

Reaction equation

HRID 1161675 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Cl[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[N:15]=[C:14]([NH2:25])[N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:17]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[N:15]=[C:14]([NH2:25])[N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 112183534-Chloro-6-(4-fluorophenyl)pyrimidin-2-amine

Product 1

HCID 112545744,6-Bis(4-fluorophenyl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of compound 4-fluoro phenyl boronic acid, compound 4-chloro-6-(4-fluoro-phenyl)-pyrimidin-2-ylamine, (PPh3)4Pd and sodium carbonate in dimethylformamide was stirred for 1 hour at 25 ° C. and then for 12 hours at 80 ° C. under nitrogen atmosphere followed by purification to yield the desired compound.

Workup

  1. customfor 12 hours at 80 ° C. under nitrogen atmosphere followed by purification

Sources & evidence

ORD record
ord-263e681cd45d4f4f9e475d63bb1f23b3
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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