HCID 67328066, compound → HCID 53373131, compound

HRID 1846175Notes

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][OH:29])=[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][OH:29])[C:9]([OH:8])=[C:14]([CH3:15])[N:13]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution containing 44.0 mg (0.11 mmol) of 10-(5-(benzyloxy)-2-(dimethylamino)-6-methylpyrimidin-4-yl)decan-1-ol in 3 mL of methanol was added 3 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/N). The reaction mixture was stirred at 23° C. under a hydrogen atmosphere for 15 min. The reaction mixture was filtered through Celite and the filtrate was concentrated under diminished pressure to afford 2-(dimethylamino)-4-(10-hydroxydecyl)-6-methylpyrimidin-5-ol as a colorless oil: yield 33 mg (100%). An analytical sample was obtained by chromatography on a silica gel column (10×1 cm). Elution with 2:1 toluene-ethyl acetate afforded the purified product as a colorless oil; silica gel TLC Rf 0.25 (2:1 toluene-ethyl acetate); 1H NMR (methanol-d4) δ1.29-1.35 (m, 12H), 1.49 (m, 2H), 1.65 (m, 2H), 2.26 (s, 3H), 2.62 (dd, 2H, J=7.2, 7.2 Hz), 3.06 (s, 6H) and 3.51 (t, 2H, J=6.4 Hz); 13C NMR (methanol-d4) δ 17.8, 25.5, 27.3, 29.13, 29.15, 29.15, 29.18, 29.3, 31.2, 32.2, 36.5, 36.5, 61.6, 138.0, 155.6, 157.3 and 159.4; mass spectrum (APCI), m/z 310.2490 (M+H)+ (C17H32N3O2 requires 310.2495).

Workup

filtrationThe reaction mixture was filtered through Celite
concentrationthe filtrate was concentrated under diminished pressure

Sources & evidence

ORD record: ord-629e4ba2f78248a6a6fe32d8ac391827
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952025B2

Reaction notes

Loading…