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

HRID 1455767Notes

Reaction equation

HRID 1455767 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-22570a7f795e43ecbc23fd107def75e9
Source dataset
uspto-grants-2009_01
Patent number
US07482350B2

Reaction notes

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