Potassium Carbonate → 4-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamide

HRID 500126Notes

Reaction equation

HRID 500126 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)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>[NH2:27][C:24]1[N:25]=[CH:26][C:21]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=2)=[CH:22][N:23]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 24694329Benzamide, 4-bromo-2-fluoro-N-methyl-

Product 1

HCID 672245484-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamideYield 91.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (900 mg, 3.9 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (710 mg, 3.2 mmol), tetrakis(triphenylphosphine)palladium (100 mg, 0.1 mmol) and potassium carbonate (1.3 g, 9.7 mmol) in toluene (6.0 mL) and ethanol (3.0 mL) and water (3.0 mL) was heated at 110° C. for 2 hours. After cooling to RT, the reaction mixture was quenched with water and extracted with diethyl ether. The solid was filtered and washed with water and diethyl ether to afford the desired product (720 mg).

Workup

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with diethyl ether
  4. filtrationThe solid was filtered
  5. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-8cdfe1f46f0c4d279f1babc658af7735
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

Loading…