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tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylate → Ethyl 4-(4-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)phenylamino)-2-chloro-6-methylpyrimidine-5-carboxylate

HRID 1025377
Notes
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Reaction equation

HRID 1025377 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 12045001tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylateHCID 215179345-Pyrimidinecarboxylic acid, 2,4-dichloro-6-methyl-, ethyl ester

Product 1

HCID 86677021Ethyl 4-(4-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)phenylamino)-2-chloro-6-methylpyrimidine-5-carboxylateYield 61.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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

  1. additionThe reaction mixture was poured onto water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes