Dichloromethane → HCID 86698565, compound

HRID 1846178Notes

Reaction equation

HRID 1846178 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](N)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OC(C)(C)C)=O.C(Cl)[Cl:39]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[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:39])=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10906Tert-Butyl nitriteHCID 67328269HCID 67328269, compound

Product 1

HCID 86698565HCID 86698565, compound

Reagents, catalysts & solvents 1

HCID 5963Benzyltrimethylammonium chlorideCatalyst

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 240 mg (0.58 mmol) of 5-(benzyloxy)-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidin-2-amine in 10 mL of anhydrous DCM were added 1.10 g (5.80 mmol) of benzyltrimethylammonium chloride followed by 696 μL (5.80 mmol) of t-butyl nitrite. The reaction mixture was stirred at 23° C. protected from light for 15 h. The mixture was filtered and the filtrate was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (3×10 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as a colorless oil: yield 44 mg (16%); silica gel TLC Rf 0.45 (4:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.24 (br s, 12H), 1.55 (quint, 2H, J=7.2 Hz), 1.65 (quint, 2H, J=6.8 Hz), 2.42 (s, 3H), 2.67 (dd, 2H, J=8.0, 8.0 Hz), 3.33 (s, 3H), 3.47 (t, 2H, J=6.8 Hz), 4.59 (s, 2H), 4.83 (s, 2H) and 7.37 (m, 5H); 13C NMR (CDCl3) δ 19.32, 26.16, 28.14, 29.25, 29.35, 29.35, 29.47, 29.51, 29.71, 31.92, 55.04, 67.85, 76.03, 96.36, 128.08, 128.73, 128.73, 128.77, 128.77, 135.73, 149.01, 154.24, 163.79 and 167.41; mass spectrum (APCI), m/z (M+H)+435.2411 (C24H36N2O3Cl requires 435.2415)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under diminished pressure
  3. customThe residue was purified by chromatography on a silica gel column (3×10 cm)
  4. washElution with 4:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-2bc789e25fdd43efb275a56b566954b2
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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