Potassium Phosphate, Tribasic → HCID 67337889, compound

HRID 1909142Notes

Reaction equation

HRID 1909142 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C=O)C.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([C:17]3[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=3)[N:3]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 67337889HCID 67337889, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2,6-dichloropyrimidine-4-carboxylate (0.39 g, 1.87 mmol) in DMF (15 mL) were added (4-methylphenyl)boronic acid (0.84 g, 6.17 mmol), potassium phosphate tribasic (0.79 g, 3.74 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.15 g, 0.19 mmol). The mixture was heated to 80° C. After 16 h, the mixture was cooled to ambient temperature. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate) gave the title compound (0.31 g). MS 319.2 (M+1).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-48496cd602b0459e8b67b1812951372e
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

Loading…