Sodium Carbonate → HCID 18438114, compound

HRID 1643208Notes

Reaction equation

HRID 1643208 reaction equation
[CH2:1]([C:5]1[C:6](Cl)=[N:7][C:8]([Cl:12])=[N:9][C:10]=1[CH3:11])[CH2:2][CH2:3][CH3:4].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.[H][H].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>[CH2:1]([C:5]1[C:10]([CH3:11])=[N:9][C:8]([Cl:12])=[N:7][C:6]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 18438113HCID 18438113, compound

Product 1

HCID 18438114HCID 18438114, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 178467616HCID 178467616, compoundSolvent

Procedure

A mixture of 5-butyl-2,4-dichloro-6-methyl-pyrimidine (711 mg, 3.24 mmol), phenylboronic acid (475 mg, 3.89 mmol), Na2CO3 (1.03 g, 9.73 mmol), and Pd(PPh3)4 (187 ma, 0.162 mmol) in toluene-EtOH—H2 (4 ml-0.5 ml-2 mL) is stirred at reflux for 6 hours. After cooling, the reaction mixture is diluted with H2O and extracted with EtOAc. The extract is then washed with brine, dried over Na2SO4, and concentrated. The residue is purified by flash chromatography on silica gel. Elution with 8:1 hexanes-EtOAc followed by 7:1 hexanes-EtOAc affords 5-butyl-2-chloro-4-methyl-6-phenyl-pyrimidine as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.45 (m, 5H), 2.65-2.62 (m, 2H), 2.60 (s, 3H), 1.46-1.36 (m, 2H), 1.25 (sext, J=7.2 Hz, 2H), 0.81 (t, J=7.2 Hz, 3H) ppm.

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. washThe extract is then washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography on silica gel
  8. washElution with 8:1 hexanes-EtOAc

Sources & evidence

ORD record
ord-f53cb02e92ea4eda9d58ded9ea5cd595
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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