HCID 67328968, compound → HCID 53373264, compound

HRID 1846192Notes

Reaction equation

HRID 1846192 reaction equation
C([O:8][C:9]1[C:10]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[N:11][C:12]([N:16]([CH3:18])[CH3:17])=[N:13][C:14]=1[CH3:15])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:18][N:16]([CH3:17])[C:12]1[N:11]=[C:10]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:9]([OH:8])=[C:14]([CH3:15])[N:13]=1

Participants

4

Reactant 1

HCID 67328968HCID 67328968, compound

Product 1

HCID 53373264HCID 53373264, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 100 mg (0.21 mmol) 5-(benzyloxy)-4-hexadecyl-N,N,6-trimethylpyrimidin-2-amine in 5 mL of methanol were added 5 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/E). The reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min. The reaction mixture was filtered through celite and the filtrated was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (8×3 cm). Elution with 4:1 hexane-ethyl acetate afforded the expected product as white solid: yield 20 mg (25%); mp: 86-87° C.; silica gel TLC Rf 0.45 (4:1 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 0.89 (t, 3H, J=6.8 Hz), 1.28-1.34 (m, 26H), 1.67 (quint, 2H, J=7.2 Hz), 2.28 (s, 3H), 2.63 (dd, 2H, J=7.6, 7.6 Hz) and 3.07 (s, 6H); 13C NMR (methanol-d4) δ 12.96, 17.52, 22.27, 27.23, 29.00, 29.12, 29.12, 29.20, 29.20, 29.20, 29.30, 29.30, 29.30, 29.30, 29.30, 31.21, 31.61, 36.50, 36.50, 138.02, 155.61, 157.31 and 159.41; mass spectrum (APCI), m/z 378.3491 (M+H)+ (C23H44N3O requires 378.3484).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrated was concentrated under diminished pressure
  3. customThe residue was purified by chromatography on a silica gel column (8×3 cm)
  4. washElution with 4:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-cf0204bc320547bb88906a6509f96f9e
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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