Water → HCID 69048427, compound

HRID 733166Notes

Reaction equation

HRID 733166 reaction equation
C(=O)([O-])[O-].[K+].[K+].O.Cl[C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][CH3:17])[N:12]=[C:11]([S:18]([CH3:21])(=[O:20])=[O:19])[N:10]=1.[CH:22]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)([CH3:24])[CH3:23]>C(COC)OC.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>[CH:22]([C:25]1[CH:30]=[C:29]([C:9]2[CH:14]=[C:13]([CH2:15][CH2:16][CH3:17])[N:12]=[C:11]([S:18]([CH3:21])(=[O:20])=[O:19])[N:10]=2)[CH:28]=[CH:27][CH:26]=1)([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27734783-Isopropylbenzeneboronic acidHCID 86619633HCID 86619633, compound

Product 1

HCID 69048427HCID 69048427, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Potassium carbonate (0.850 g, 6 mmol), water (1 ml) and tetrakis(triphenylphosphine)palladium (0.695 g, 0.6 mmol) were successively added under a nitrogen atmosphere, to a mixture of 4-chloro-2-methanesulfonyl-6-propyl-pyrimidine (1.17 g, 5 mmol) and 3-isopropyl-phenylboronic acid (0.984 g, 6 mmol) in dimethoxyethane (40 mL). The mixture was refluxed for 18 hours then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: Cyclohexane/Ethyl acetate 7/3) to afford a yellow oil which crystallised in pentane. After filtration, 4-(3-isopropyl-phenyl)-2-methanesulfonyl-6-propyl-pyrimidine (0.380 g) was obtained as an off white solid (mp=82° C.).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed over silica gel (eluent: Cyclohexane/Ethyl acetate 7/3)
  9. customto afford a yellow oil which
  10. customcrystallised in pentane
  11. filtrationAfter filtration

Sources & evidence

ORD record
ord-eb011ff728b74ea9baef984b3506d68c
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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