Hydrazine → 4-(4-Chlorophenyl)-6-hydrazinyl-2-(methylthio)-5-phenylpyrimidine

HRID 271418Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:5]=[C:4]([S:21][CH3:22])[N:3]=1.[NH2:23][NH2:24]>C1COCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:6]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:2]([NH:23][NH2:24])[N:3]=[C:4]([S:21][CH3:22])[N:5]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 4-chloro-6-(4-chlorophenyl)-2-(methylthio)-5-phenylpyrimidine (1.22 g, 3.52 mmol) in THF (15 mL) at room temperature under argon was added H2NNH2 (340 mg, 10.5 mmol). The reaction mixture was heated at 60° C. under argon for 2 h. Analysis by HPLC/MS indicated that the reaction was complete. The solvent was evaporated, and the resulting residue was coevaporated with toluene (2×5 mL) and then dichloromethane (2×10 mL), then dried under vacuum. The crude title compound was used directly in the next step. HPLC/MS: retention time=2.73 min, [M+H]30 =343.

Workup

customThe solvent was evaporated
dry with materialdichloromethane (2×10 mL), then dried under vacuum

Sources & evidence

ORD record: ord-c444a421c2ea41e3a869d35d60b7a34f
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452892B2

Reaction notes

Loading…