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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
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HRID 1025377 반응식
[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]
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4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-17963f407eab43f8a0b102386b0edbac
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729079B2

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