Thionyl Chloride → 2-(2,6-Diethylphenyl)-4-methoxy-6-methyl-5-(1-propylbutenyl)pyrimidine

HRID 1091949Notes

Reaction equation

HRID 1091949 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([C:19](O)([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])=[C:13]([CH3:27])[N:12]=1)[CH3:2].O=S(Cl)Cl>N1C=CC=CC=1>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([C:19]([CH2:23][CH2:24][CH3:25])=[CH:20][CH2:21][CH3:22])=[C:13]([CH3:27])[N:12]=1)[CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 575314274-[2-(2,6-Diethylphenyl)-4-methoxy-6-methylpyrimidin-5-yl]heptan-4-ol

Product 1

HCID 665898042-(2,6-Diethylphenyl)-4-methoxy-6-methyl-5-(1-propylbutenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-[2-(2,6-diethylphenyl)-4-methoxy-6-methylpyrimidin-5-yl]heptan-4-ol (0.6 g, 1.7 mmol) in anhydrous pyridine (10 mL) is added 1.5 mL of SOCl2 dropwise under nitrogen. The reaction mixture is stirred at room temperature for 3 h, quenched with a saturated aqueous NaHCO3 solution and extracted with DCM. The organic layer is washed with water, brine, dried over Na2SO4, and concentrated. The residue is purified by flash chromatography eluting with 10% EtOAc-hexanes to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 7.24-7.29 (m, 1H), 7.13 (d, J=9 Hz, 2H), 5.39 (t, J=7.5. Hz, 1H), 3.91 (s,3H), 2.46 (s,3H),2.24-2.43 (m, 6H), 1.28-1.33 (m,4H), 1.10 (q, J=7.8, 4.8 Hz, 6H), 0.91 (t, j=7.2 Hz, 6H); LC-MS found 352 (MH+).

Workup

  1. customquenched with a saturated aqueous NaHCO3 solution
  2. extractionextracted with DCM
  3. washThe organic layer is washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography
  7. washeluting with 10% EtOAc-hexanes

Sources & evidence

ORD record
ord-05ca3b8f92324a23b9416a7a48f48047
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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