Potassium Carbonate → 4-(3-amino-1,2,4-triazin-6-yl)-N,2-dimethylbenzamide

HRID 452042Notes

Reaction equation

[CH3:1][NH:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]=1[CH3:19].Br[C:22]1[N:27]=[N:26][C:25]([NH2:28])=[N:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:28][C:25]1[N:26]=[N:27][C:22]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:2][CH3:1])=[O:20])=[C:5]([CH3:19])[CH:6]=2)=[CH:23][N:24]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of N,2-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Step 2, 0.3 g, 0.001 mol), 6-bromo-1,2,4-triazin-3-amine (0.21 g, 1.2 mmol, Example 2, Step 1), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol) and potassium carbonate (0.45 g, 3.3 mmol) in toluene (1.9 mL), ethanol (0.94 mL) and water (0.94 mL). The resulting mixture was heated at 130° C. for 2.5 h. The mixture was diluted with MeOH, filtered, and washed with DCM/methanol (90%). The filtrate was concentrated. The residue was purified by flash chromatography on a silica gel column with 10% MeOH in DCM to afford the desired product (110 mg, 41%). LCMS (M+H)+: m/z=244.3.

Workup

filtrationfiltered
washwashed with DCM/methanol (90%)
concentrationThe filtrate was concentrated
customThe residue was purified by flash chromatography on a silica gel column with 10% MeOH in DCM

Sources & evidence

ORD record: ord-abc0bf1818d4434e95d3f929d6adc733
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487096B2

Reaction notes

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