Piperazine → 4-(Piperazin-1-yl)-6-(3-methyl-4-methoxyphenyl)-pyrido[3,2-d]pyrimidine

HRID 1517416Notes

Reaction equation

Cl[C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([CH3:20])[CH:13]=3)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(O)(C)C>[N:21]1([C:2]2[C:3]3[N:11]=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([CH3:20])[CH:13]=4)[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 4-chloro-6-(3-methyl-4-methoxyphenyl)-pyrido[3,2-d]pyrimidine (0.99 mmole) in isopropanol (40 ml) was added piperazine (1.99 mmole). The reaction mixture was heated at 80° C. for 2 hours. The solvents were evaporated in vacuo. The crude residue was purified by silica gel flash chromatography (the mobile phase being a mixture of methanol and dichloromethane with an 0.5% aqueous NH3 solution (in a ratio gradually ranging from 2:98 to 3:97), resulting in the pure title compound (259 mg, yield 78%) which was characterized by its mass spectrum as follows: MS (m/z): 336 ([M+H]+, 100).

Workup

customThe solvents were evaporated in vacuo
customThe crude residue was purified by silica gel flash chromatography (the mobile phase
additiona mixture of methanol and dichloromethane with an 0.5% aqueous NH3 solution (in a ratio

Sources & evidence

ORD record: ord-c8c377a8436841ae96d8ffc026a12d08
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232278B2

Reaction notes

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