Sodium methanethiolate → 2-Methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine

HRID 1621366Notes

Reaction equation

HRID 1621366 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[CH:10]=[C:9]([Sn:11]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]([CH3:24])[N:6]=1>O1CCCC1.O>[CH3:24][C:7]1[N:6]=[C:5]([S:2][CH3:1])[CH:10]=[C:9]([Sn:11]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 866470454-Chloro-2-methyl-6-(tributylstannyl)pyrimidine

Product 1

HCID 595482802-Methyl-4-(methylthio)-6-(tributylstannyl)pyrimidineYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium thiomethoxide (140 mg, 2 mmol) was added to 4-chloro-2-methyl-6-(tributylstannyl)pyrimidine (835 mg, 2 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as an orange oil. The crude product was purified by silica gel chromatography, eluting with 5% EtOAc/hexanes to give 2-methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine (256 mg, 30% yield). 1H NMR (300 MHz, CDCl3) δ 7.07 (s, 1H); 2.62 (s, 3H); 2.51 (s, 3H); 1.44-1.70 (m, 6H); 1.21-1.42 (m, 6H); 0.98-1.21 (m, 6H); 0.91 (t, 9H).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated NaCl (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material as an orange oil
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-34fb1bcf92a2488fbce1d10539186773
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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