tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylate → HCID 86677021, compound

HRID 1025377Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([CH3:14])[N:3]=1.[NH2:15][C:16]1[CH:35]=[CH:34][C:19]([CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[CH:18][CH:17]=1>CN1C(=O)CCC1>[C:30]([O:29][C:27]([N:24]1[CH2:23][CH2:22][N:21]([CH2:20][C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:6]3[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([CH3:14])[N:3]=[C:2]([Cl:1])[N:7]=3)=[CH:35][CH:34]=2)[CH2:26][CH2:25]1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (0.5 g, 2.1 mmol) and tert-butyl 4-(4-aminobenzyl)piperazine-1-carboxylate (0.6 g, 2.06 mmol) were dissolved in NMP and stirred at 0° C. for 2 hour. The reaction mixture was poured onto water and extracted with EtOAc. The organic layer was washed with water, dried over Na2SO4 and evaporated under vacuum to get the desired compound (0.62 g). 1H NMR (400 MHz, CDCl3): δ 10.58 (s, 1H), 7.58 (d, J=6.4 Hz, 2H), 7.31 (d, J=6.4 Hz, 2H), 4.45 (q, J=6.8 Hz, 2H), 3.56 (s, 2H), 3.41 (m, 4H), 2.69 (s, 3H), 2.47 (m, 4H), 1.45 (s, 9H), 1.43 (t, J=6.8 Hz, 3H); MS m/z 490.0 (M+1).

Workup

additionThe reaction mixture was poured onto water
extractionextracted with EtOAc
washThe organic layer was washed with water
dry with materialdried over Na2SO4
customevaporated under vacuum

Sources & evidence

ORD record: ord-17963f407eab43f8a0b102386b0edbac
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729079B2

Reaction notes

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