HCID 67328276, compound → HCID 53373263, compound

HRID 1846188Notes

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][CH3:28])=[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]>[CH2:19]([C:10]1[C:9]([OH:8])=[C:14]([CH3:15])[N:13]=[C:12]([N:16]([CH3:18])[CH3:17])[N:11]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution containing 150 mg (0.48 mmol) 5-(benzyloxy)-4-decyl-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 33 mg (28%); mp: 71-72° C.; silica gel TLC Rf 0.25 (4:1 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 0.87 (t, 3H, J=6.8 Hz), 1.21-1.31 (m, 14H), 1.65 (quint, 2H, J=7.2 Hz), 2.26 (s, 3H), 2.62 (dd, 2H, J=7.2, 7.2 Hz) and 3.05 (s, 6H); 13C NMR (methanol-d4) δ 13.01, 17.55, 22.29, 27.27, 29.02, 29.15, 29.17, 29.26, 29.29, 31.24, 31.64, 36.52, 36.52, 138.04, 155.59, 157.31 and 159.41; mass spectrum (APCI), m/z 294.2554 (M+H)+ (C17H32N3O requires 294.2545).

Workup

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

Sources & evidence

ORD record: ord-ef436b5e94584929b3d207f23d8b1c92
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952025B2

Reaction notes

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