HCID 67329641, compound → HCID 53373262, compound

HRID 1846184Notes

Reaction equation

C([O:8][C:9]1[C:10]([CH3:23])=[N:11][C:12]([N:20]([CH3:22])[CH3:21])=[N:13][C:14]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:22][N:20]([CH3:21])[C:12]1[N:11]=[C:10]([CH3:23])[C:9]([OH:8])=[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:13]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution containing 150 mg (0.48 mmol) of 5-(benzyloxy)-N,N,4-trimethyl-6-pentylpyrimidin-2-amine in 5 mL of methanol were added 5 mg of 20% palladium hydroxide on carbon (Degussa typy 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 2:1 hexane-ethyl acetate afforded the expected product as white solid: yield 60 mg (56%); mp: 61-62° C.; silica gel TLC Rf 0.50 (2:1 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 0.89 (t, 3H, J=5.6 Hz), 1.33 (m, 4H), 1.66 (quint, 2H, J=7.2 Hz), 2.26 (s, 3H), 2.62 (dd, 2H, J=7.6, 7.6 Hz) and 3.05 (s, 6H); 13C NMR (methanol-d4) δ 12.93, 17.53, 22.16, 27.00, 31.21, 31.43, 36.49, 138.01, 155.64, 157.33 and 159.44; mass spectrum (APCI), m/z 224.1769 (M+H)+ (C12H22N30 requires 224.1763).

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 2:1 hexane-ethyl acetate

Sources & evidence

ORD record: ord-092a2f9ffd2c4a57a923697c79548c6d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952025B2

Reaction notes

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