2-Amino-4,6-dimethylpyridine → Ethyl 6-chloro-4-(4,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate

HRID 1396392Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([NH2:22])[CH:16]=1>C(#N)C>[Cl:8][C:6]1[N:5]=[N:4][C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:2]([NH:22][C:17]2[CH:16]=[C:15]([CH3:14])[CH:20]=[C:19]([CH3:21])[N:18]=2)[CH:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of ethyl 4,6-dichloropyridazine-3-carboxylate (790 mg, 3.57 mmol) in acetonitrile (11.9 mL) was added 4,6-dimethylpyridin-2-amine (873 mg, 7.15 mmol) and heated at 140° C. in a sealed vial for 20 h. The mixture was concentrated in vacuo then purified by chromatography (silica, 0-8% acetone in dichloromethane) to give ethyl 6-chloro-4-(4,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate (165 mg, 538 μmol, 15%) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.60 (s, 1H), 9.24 (s, 1H), 8.75 (s, 1H), 8.59 (s, 1H), 4.58 (q, J=7.1 Hz, 2H), 2.53 (s, 3H), 2.33 (s, 3H), 1.52 (t, J=7.1 Hz, 3H); MS (EI/CI) m/z: 306.1 [M+H].

Workup

concentrationThe mixture was concentrated in vacuo
customthen purified by chromatography (silica, 0-8% acetone in dichloromethane)

Sources & evidence

ORD record: ord-70162641ddd048bc8f1538f355131841
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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