Methanol → HCID 67329649, compound

HRID 1846179Notes

Reaction equation

HRID 1846179 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][O:29][CH3:30])=[N:11][C:12](Cl)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[CH3:32][OH:33]>>[CH2:1]([O:8][C:9]1[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][O:29][CH3:30])=[N:11][C:12]([O:33][CH3:32])=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 86698565HCID 86698565, compound

Product 1

HCID 67329649HCID 67329649, compound

Procedure

To a stirred solution containing 41.0 mg (0.09 mmol) of 5-(benzyloxy)-2-chloro-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidine in 5 mL of anhydrous methanol were added 22 mg (0.94 mmol) of sodium. The mixture was then stirred at reflux for 16 h. The reaction was quenched with water and poured into 50 mL of water. The mixture was extracted with two 50-mL portions of ethyl acetate. The combined organic solution was washed with one 50-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (2×6 cm). Elution with 1:1 hexanes-ethyl acetate afforded the expected product as a colorless oil: yield 30 mg (74%); silica gel TLC Rf 0.65 (1:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.24 (br m, 12H), 1.55 (quint, 2H, J=6.8 Hz), 1.68 (quint, 2H, J=7.6 Hz), 2.37 (s, 3H), 2.65 (dd, 2H, J=7.6, 7.6 Hz), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.93 (s, 3H), 4.59 (s, 2H), 4.83 (s, 2H) and 7.37 (m, 5H); 13C NMR (CDCl3) δ 19.21, 26.16, 27.85, 29.36, 29.40, 29.51, 29.53, 29.71, 31.71, 54.69, 55.02, 67.85, 75.80, 96.36, 127.49, 128.38, 128.38, 128.63, 128.63, 136.50, 145.14, 160.61, 162.38 and 165.87; mass spectrum (APCI), m/z (M+H)+431.2910 (C25H39N2O4 requires 431.2910).

Workup

  1. temperatureat reflux for 16 h
  2. customThe reaction was quenched with water
  3. additionpoured into 50 mL of water
  4. extractionThe mixture was extracted with two 50-mL portions of ethyl acetate
  5. washThe combined organic solution was washed with one 50-mL portion of brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under diminished pressure
  8. customThe residue was purified by chromatography on a silica gel column (2×6 cm)
  9. washElution with 1:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-eee3e0d0c17842e6ba0a0e3e5d07237d
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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