2-(1-Benzyloxy-ethyl)-7-(3,6-dihydro-2H-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one → 2-(1-Hydroxy-ethyl)-7-(tetrahydro-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one

HRID 57732Notes

Reaction equation

C([O:8][CH:9]([C:11]1[NH:16][C:15](=[O:17])[C:14]2=[CH:18][N:19]=[C:20]([C:21]3[CH2:22][CH2:23][O:24][CH2:25][CH:26]=3)[N:13]2[N:12]=1)[CH3:10])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:8][CH:9]([C:11]1[NH:16][C:15](=[O:17])[C:14]2=[CH:18][N:19]=[C:20]([CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[N:13]2[N:12]=1)[CH3:10]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of compound 13 (900 mg, 2.55 mmol) in MeOH (30 mL) was added Pd(OH)2/C (120 mg). The mixture was stirred at 75° C. under H2 (50 psi) overnight. The suspension was filtered through Celite, washed with MeOH (20 mL×2). The combined organic phases were concentrated in vacuo to afford compound 14 (540 mg, 80% yield) as a white solid. LC-MS: m/z 265 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 9.07 (br. s, 1H), 7.85 (s, 1H), 4.84 (q, J=6.4 Hz, 1H), 4.11 (m, 2H), 3.59 (m, 2H), 3.44˜3.39 (m, 1H), 2.14˜2.06 (m, 3H), 1.92˜1.88 (m, 2H), 1.64 (d, J=6.4 Hz, 3H).

Workup

filtrationThe suspension was filtered through Celite
washwashed with MeOH (20 mL×2)
concentrationThe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record: ord-0a3948b53ba14742ac99520fb7c55a41
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434733B2

Reaction notes

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