Sodium Carbonate → HCID 18438114, compound

HRID 457376Notes

Reaction equation

HRID 457376 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.C(O)C.O.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 86587398Ethanol toluene waterSolvent

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 mg, 0.162 mmol) in toluene-EtOH—H2O (4 ml-0.5 ml-2 mL) is stirred at relux 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. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. washThe extract is then washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography on silica gel
  7. washElution with 8:1 hexanes-EtOAc

Sources & evidence

ORD record
ord-ac1d491c5797495ab19fd836a13f9f1b
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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