1,1'-Carbonyldiimidazole → 7-Methyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazin-4(1H)-one

HRID 1498020Notes

Reaction equation

[CH3:1][C:2]1[N:3]([NH:13][CH:14]=[NH:15])[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][N:10]([CH3:12])[CH:11]=2)[N:6]=1.[C:16](N1C=CN=C1)(N1C=CN=C1)=[O:17]>O1CCCC1>[CH3:1][C:2]1[N:3]2[C:4]([C:16](=[O:17])[NH:15][CH:14]=[N:13]2)=[C:5]([C:7]2[CH:8]=[N:9][N:10]([CH3:12])[CH:11]=2)[N:6]=1

Participants

Conditions

Temperature: 65 °C

Procedure

N-[2-Methyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl]imidoformamide (58.3 g, 285 mmol) was combined with 1,1′-carbonyldiimidazole (98%, 59.0 g, 357 mmol) in tetrahydrofuran (1140 mL) at 63° C., and the suspension was stirred for 2.5 hours at 65° C. The mixture was cooled and concentrated in vacuo; the resulting solid was slurried with methanol (400 mL), warmed to reflux for 20 minutes and cooled to 7° C. The solid was collected to provide C1 as a pale yellow solid. Yield: 45.9 g, 199 mmol, 70%. LCMS m/z 231.1 (M+1). 1H NMR (500 MHz, DMSO-d6) δ 2.48 (s, 3H), 3.88 (s, 3H), 7.79 (s, 1H), 8.08 (s, 1H), 8.37 (s, 1H), 11.59 (br s, 1H).

Workup

temperatureThe mixture was cooled
concentrationconcentrated in vacuo
temperaturewarmed
temperatureto reflux for 20 minutes
temperaturecooled to 7° C
customThe solid was collected

Sources & evidence

ORD record: ord-ea274d4486294b82b7296b78bccce7b5
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09200000B2

Reaction notes

Loading…