Sodium Carbonate → 4-Ethyl-6-(4-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-3,4-dihydro-pyrazino[2,3-b]pyrazin-2(1H)-one

HRID 1047282Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[N:11]([CH2:12][CH3:13])[CH2:10][C:9](=[O:14])[NH:8][C:5]2=[N:6][CH:7]=1.[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[N:21]1[CH:25]=[N:24][N:23]=[C:22]1[C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[CH2:12]([N:11]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:29]3[CH:30]=[CH:31][C:26]([C:22]4[N:21]([CH:16]5[CH2:17][CH2:18][CH2:19][CH2:20][O:15]5)[CH:25]=[N:24][N:23]=4)=[CH:27][CH:28]=3)[N:3]=2)[NH:8][C:9](=[O:14])[CH2:10]1)[CH3:13]

Participants

Conditions

Temperature: 120 °C

Procedure

6-Bromo-4-ethyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (1.1 equiv), 4-(tetrahydro-2H-pyran-2-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-1,2,4-triazole (1 equiv) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloromethane (0.05 equiv) were combined in 1,4-dioxane followed by the addition of sodium carbonate (3 equiv) in water. The solution was heated in a Biotage Emrys Optimizer microwave reactor to 120° C. for 30 min. The solution was condensed under reduced pressure and purified using column chromatography (0-10% methanol in ethyl acetate) to afford the title compound in 45% yield. MS (ESI) m/z 406.6 [M+1]+.

Workup

customcondensed under reduced pressure
custompurified

Sources & evidence

ORD record: ord-326fa82631b542aea868db326a1559ce
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569494B2

Reaction notes

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