Potassium Carbonate → HCID 58415713, compound

HRID 44896Notes

Reaction equation

[CH2:1]([CH:3]1[N:12]([C:13]2[CH:14]=[N:15][NH:16][CH:17]=2)[C:11]2[N:10]=[C:9]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:8]=[CH:7][C:6]=2[N:5]([CH3:30])[C:4]1=[O:31])[CH3:2].[C:32]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cl-].[Na+].O>[CH2:1]([CH:3]1[N:12]([C:13]2[CH:14]=[N:15][N:16]([CH3:32])[CH:17]=2)[C:11]2[N:10]=[C:9]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:8]=[CH:7][C:6]=2[N:5]([CH3:30])[C:4]1=[O:31])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

7-ethyl-2-(2-(4-fluorophenyl)-1H-imidazol-1-yl)-5-methyl-8-(1H-pyrazol-4-yl)-7,8-dihydropteridin-6(5H)-one (Example 331, 55 mg, 0.131 mmol) was dissolved in 3 mL of dioxane and Me3PO4 (37 mg, 0.262 mmol) and K2CO3 (90 mg, 0.655 mmol) were added and the reaction mixture was stirred for 18 h at 90° C. The reaction mixture was diluted with brine and extracted with EtOAc. The organic phase was dried with Na2SO4, filtered, concentrated under vacuum and purified by HPLC to give the title compound (7.6 mg). 1H-NMR (CDCl3, 400 MHz): δ: 7.91 (s, 1H), 7.71 (s, 1H), 7.50-7.60 (m, 3H), 7.12 (s, 1H), 7.08-7.10 (m, 2H), 7.01 (s, 1H), 4.57-4.61 (m, 1H), 3.79 (s, 3H), 3.46 (s, 3H), 1.82-1.98 (m, 1H), 1.78-1.82 (m, 1H), 0.82 (t, 3H, J=7.4 Hz); LCMS: 433.2 m/z (M+H)+; ret. Time: 4.36 min (Analytical Method C).

Workup

extractionextracted with EtOAc
dry with materialThe organic phase was dried with Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
custompurified by HPLC

Sources & evidence

ORD record: ord-fe6fadc9830d40fdbe2e4e36f27aaf61
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541418B2

Reaction notes

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