Sodium Carbonate → 6-[1-(1-Ethoxyethyl)-1H-pyrazol-4-yl]-1,2,4-triazin-3-amine

HRID 500237Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[N:13]=[N:12][C:11]([NH2:14])=[N:10][CH:9]=1.[CH2:15]([O:17][CH:18]([N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1)[CH3:19])[CH3:16]>O.C1(C)C=CC=CC=1.C(O)C.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>[CH2:15]([O:17][CH:18]([N:20]1[CH:24]=[C:23]([C:8]2[N:13]=[N:12][C:11]([NH2:14])=[N:10][CH:9]=2)[CH:22]=[N:21]1)[CH3:19])[CH3:16]

Participants

Conditions

Temperature: 110 °C

Procedure

Sodium carbonate (510 mg, 4.8 mmol) in water (1 mL) was added to a mixture of 6-bromo-1,2,4-triazin-3-amine (0.420 g, 2.40 mmol), 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.766 g, 2.88 mmol), and tetrakis(triphenylphosphine)palladium (100 mg, 0.1 mmol) in toluene (7 mL) and ethanol (5 mL). The resulting mixture was heated at 110° C. for 2 h. The mixture was cooled to RT, diluted with water, and extracted with chloroform. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was treated with CH2Cl2/Et2O and filtered to give the desired product (0.39 g, 69%). LCMS: (M+H)=235.4.

Workup

temperatureThe mixture was cooled to RT
extractionextracted with chloroform
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
additionThe residue was treated with CH2Cl2/Et2O
filtrationfiltered

Sources & evidence

ORD record: ord-9999ed8e98284d5db871256409a8c210
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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