Potassium Carbonate → N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine

HRID 729341Notes

Reaction equation

CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[N:11]2)=O.[CH:17]1([NH:20][C:21]([NH2:23])=[NH:22])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:17]1([NH:20][C:21]2[N:23]=[C:5]([C:7]3[CH:8]=[N:9][N:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[N:11]4)[CH:4]=[CH:3][N:22]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 165 °C

Procedure

To a solution of (2E)-3-(dimethylamino)-1-pyrazolo[1,5-b]pyridazin-3-yl-2-propen-1-one (43 mg, 0.20 mmol) in DMF (2 mL) was added N-cyclopropylguanidine.0.5H2SO4 (160 mg, 0.80 mmol) and potassium carbonate (110 mg, 0.80 mmol). The reaction was heated at an oil bath temperature of 165° C. for about 18 hours. The mixture was cooled to RT and the solvent was removed in vacuo. The residue was dissolved in chloroform and filtered. The filtrate was purified by flash column chromatography (0-10% gradient MeOH/CH2Cl2) to give the title compound as a yellow solid (38 mg, 75%). 1H-NMR (400 MHz, d6-DMSO) δ 9.13 (dd, 1H, J=9.0, 1.6 Hz), 8.77 (s, 1H), 8.53 (dd, 1H, J=4.4, 1.6 Hz), 8.24 (d, 1H, J=5.2 Hz), 7.38 (m, 1H), 7.10 (d, 1H, J=5.2 Hz), 2.72 (m, 1H), 0.71 (m, 2H), 0.47 (m, 2H); MS (ESI) (M+H)+ 253.

Workup

temperatureThe mixture was cooled to RT
customthe solvent was removed in vacuo
dissolutionThe residue was dissolved in chloroform
filtrationfiltered
customThe filtrate was purified by flash column chromatography (0-10% gradient MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-b23a439e47614ba9a6cc1f5c5cee315f
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582630B2

Reaction notes

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