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Cesium carbonate → 5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-(piperidin-4-yl)naphthalene-1-yl)pyrimidine-2,4-diamine

HRID 2093821
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HRID 2093821 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[N:11](C3CCCCO3)[N:10]=2)[C:5]([Cl:21])=[CH:4][N:3]=1.C(OC([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]([NH2:45])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=O)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:21][C:5]1[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)=[N:7][C:2]([NH:45][C:38]2[C:39]3[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:35]([CH:32]3[CH2:31][CH2:30][NH:29][CH2:34][CH2:33]3)=[CH:36][CH:37]=2)=[N:3][CH:4]=1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 582550552,5-Dichloro-N-(5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)pyrimidin-4-amineHCID 58257106Tert-butyl 4-(4-aminonaphthalen-1-yl)piperidine-1-carboxylate

생성물 1

HCID 582571215-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-(piperidin-4-yl)naphthalene-1-yl)pyrimidine-2,4-diamine

시약·촉매·용매 2

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 8028Tetrahydrofuran용매

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온도
150 °C

실험 절차

A mixture of 2,5-dichloro-N-(5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)pyrimidin-4-amine (202.7 mg, 0.62 mmol), tert-butyl-4-(4-aminonaphthalen-1-yl)piperidine-1-carboxylate (202.0 mg, 0.62 mmol), Xantophos (35.9 mg, 0.062 mmol), padallium acetate (II) (7.0 mg, 0.031 mmol), and cesium carbonate (40.3 mg, 0.12 mmol) in 5.0 mL of THF was heated at 150° C. in a microwave reactor for 25 min. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The crude product was dissolved in 5 mL of DCM and 4 mL of TFA. This reaction mixture was stirred at room temperature for 2 h followed by concentration in vacuo. The crude product is purified by RP-HPLC to afford 5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-(piperidin-4-yl)naphthalene-1-yl)pyrimidine-2,4-diamine; ESMS m/z 434.2 (M+H+)

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe crude product was dissolved in 5 mL of DCM
  4. concentrationfollowed by concentration in vacuo
  5. customThe crude product is purified by RP-HPLC

출처 및 근거

ORD 기록
ord-6c04f04022fa4456af405244fe2034d6
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08445505B2

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