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2,4,6-Trimethylbenzyl chloride → HCID 178492802, compound

HRID 2216307
Notes
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Reaction equation

HRID 2216307 reaction equation
[Mg].[CH3:2][C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:4]=1[CH2:5]Cl.CC1C=C(C)C=C(C)C=1C[Mg]Cl.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([C:36]2[CH:37]=[N:38][C:39]([CH3:42])=[N:40][CH:41]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1>CCOCC.C1COCC1>[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([C:36]2[CH:41]([CH2:5][C:4]3[C:3]([CH3:2])=[CH:10][C:9]([CH3:11])=[CH:8][C:7]=3[CH3:12])[NH:40][C:39]([CH3:42])=[N:38][CH:37]=2)(=[O:35])=[O:34])=[CH:31][CH:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 741082,4,6-Trimethylbenzyl chlorideHCID 5462224MagnesiumHCID 21941673HCID 21941673, compoundHCID 178425038HCID 178425038, compound

Product 1

HCID 178492802HCID 178492802, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
3×
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of magnesium (240 mg, 10 mmol) and ether (20 mL) was added 2,4,6-trimethylbenzyl chloride (1.69 g, 10 mmol) in ether (20 mL) dropwise at reflux under N2. The freshly prepared solution of 2,4,6-trimethylbenzylmagnesium chloride in ether was added to a solution of 5-(4-methoxy-benzenesulfonyl)-2-methylpyrimidine (264 mg, 1.0 mmol) in THF (10 mL) dropwise at 0° C. The mixture was stirred under N2 at 0° C. for 1 h and then quenched by addition of saturated aqueous NH4Cl. The organic layer was separated and the aqueous layer was extracted three times with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (EtOAc) to provide 5-(4-methoxy-benzenesulfonyl)-2-methyl-6-(2,4,6-trimethylbenzyl)-1,6-dihydro-pyrimidine (203 mg, 51%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 7.86 (d, J=9.0 Hz, 2H), 7.45 (s, 1H), 6.99 (d, J=9.0 Hz, 2H), 6.83 (s, 2H), 4.40 (dd, J=10.8, 3.2 Hz, 1H), 3.86 (s, 3H), 2.96 (dd, J=14.2, 10.8 Hz, 1H), 2.87 (dd, J=14.2, 3.2 Hz, 1H), 2.25 (s, 6H), 2.24 (s, 3H), 1.91 (s, 3H); ESI MS m/z 399 [(M+H)+, calcd for C22H27N2O3S, 399.2].

Workup

  1. temperatureat reflux under N2
  2. customquenched by addition of saturated aqueous NH4Cl
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-2a0be911131241418fdbdf15da106603
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07112585B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes