Sodium Carbonate → HCID 178432648, compound

HRID 717173Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([C:9]2[N:13]=[CH:12][N:11](C(OC(C)(C)C)=O)[N:10]=2)=[N:6][C:7]=1[CH3:8].[CH:21]([N:24]1[C:29]2=[N:30][C:31](B3OC(C)(C)C(C)(C)O3)=[CH:32][N:33]=[C:28]2[NH:27][CH2:26][C:25]1=[O:43])([CH3:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>CC(N(C)C)=O.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:21]([N:24]1[C:29]2=[N:30][C:31]([C:2]3[C:7]([CH3:8])=[N:6][C:5]([C:9]4[NH:13][CH:12]=[N:11][N:10]=4)=[CH:4][CH:3]=3)=[CH:32][N:33]=[C:28]2[NH:27][CH2:26][C:25]1=[O:43])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

7-Bromo-1-isopropyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (1 equiv), bis(pinacolato)diboron) (1 equiv), potassium acetate (3 equiv) and bis(1,1′-bis(diphenylphosphino)ferrocene)palladium (0.01 equiv) were combined in dioxane, degassed with nitrogen and heated to 95° C. under nitrogen. Dilution with ethyl acetate, filtration through Celite, concentration, trituration with ethyl acetate and hexanes, filtration and drying gave the boronate ester in 60% yield. tert-Butyl 3-(5-bromo-6-methylpyridin-2-yl)-1H-1,2,4-triazole-1-carboxylate (1 equiv), 1-isopropyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (1.2 equiv), tetrakis(triphenylphosphine) palladium(0) (0.05 equiv), sodium carbonate (3 equiv) were combined in (3:1) dimethyl acetamide and water. The mixture was degassed and heated to 100° C. overnight. Standard ethyl acetate/water work up and subsequent trituration in ethyl acetate gave the desired product in 41% yield.

Workup

customThe mixture was degassed

Sources & evidence

ORD record: ord-50f598c58882471288cbd707c53feb1d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193692B2

Reaction notes

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