Potassium Carbonate → 4-(2-Aminopyrimidin-5-yl)-2,3-difluorobenzoic acid

HRID 1257919Notes

Reaction equation

HRID 1257919 reaction equation
OB(O)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:12])[C:4]=1[F:13].Br[C:16]1[CH:17]=[N:18][C:19]([NH2:22])=[N:20][CH:21]=1.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>[NH2:22][C:19]1[N:20]=[CH:21][C:16]([C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:12])[C:4]=2[F:13])=[CH:17][N:18]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 532167464-Borono-2,3-difluorobenzoic acid

Product 1

HCID 672252574-(2-Aminopyrimidin-5-yl)-2,3-difluorobenzoic acid

Reagents, catalysts & solvents 4

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

Conditions

Temperature
110 °C

Procedure

A mixture of 4-(dihydroxyboryl)-2,3-difluorobenzoic acid (0.47 g, 2.3 mmol), 5-bromopyrimidin-2-amine (0.44 g, 2.6 mmol), tetrakis(triphenylphosphine)palladium (0.1 g, 0.1 mmol), and potassium carbonate (0.96 g, 7.0 mmol) in toluene (4.0 mL), ethanol (2.0 mL) and water (2.0 mL) was heated at 110° C. for 3 h. After cooling to RT, the mixture was washed with ether to remove impurity. The aqueous layer was adjusted to pH 6 with 1N HCl. The solid was filtered, washed with water and ether to give the desired product. LCMS: (M+H)=252.9.

Workup

  1. temperatureAfter cooling to RT
  2. washthe mixture was washed with ether
  3. customto remove impurity
  4. filtrationThe solid was filtered
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-2802831dbb3b4c30899ffe359cf7374b
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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