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

HRID 1179124Notes

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-89f60296899c424b9f460937c1391877
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279473B2

Reaction notes

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