2-Hydrazinylpyrimidine → HCID 71260694, compound

HRID 2202154Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][C:11]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=O)=S)=[CH:4][CH:3]=1.[NH:26]([C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[NH2:27].C([O-])(=O)C.[Na+]>O1CCOCC1.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:10]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[N:26]([C:28]3[N:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[N:27]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-{[(4-fluorophenyl)carbonothioyl]-carbamoyl}piperidine-1-carboxylate (0.37 g, 1.01 mmol) was mixed with 2-hydrazinylprimidine (0.13 g, 1.21 mmol) and sodium acetate (0.099 g, 1.21 mmol) in 3 ml of 1,4-dioxane and acetic acid (1:1). After heating at 80° C. for 45 min, the solvents were removed under vacuum. The resulting residue was re-dissolved in dichloromethane and washed with saturated sodium bicarbonate solution and water. The organic layers were concentrated, and the residue was purified by column chromatography using a gradient of 0˜50% ethyl acetate in hexanes. LC-MS (m/z): 369.10 [M−56+H]+, 447.14 [M+Na+H]+. 1HNMR (CDCl3, 500 MHz): δ 8.92 (d, J=4.8 Hz, 2H), 8.25-8.28 (m, 2H), 7.38 (t, J=4.8 Hz, 1H), 7.15 (t, J=8.7 Hz, 2H), 4.24-4.27 (br, 2H), 3.94-4.00 (m, 2H), 2.91-2.96 (br, 2H), 2.00-2.10 (br, 4H), 1.52 (s, 9H).

Workup

customthe solvents were removed under vacuum
dissolutionThe resulting residue was re-dissolved in dichloromethane
washwashed with saturated sodium bicarbonate solution and water
concentrationThe organic layers were concentrated
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-3a6e3851060944c7b8c3429b63289b8b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365539B2

Reaction notes

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