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Sodium Carbonate → 5-(4-Amino-3-cyclohex-1-enyl-phenyl)-tetrahydro-pyrimidin-2-one

HRID 340543
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HRID 340543 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][NH:18][C:17](=[O:20])[NH:16][CH2:15]2)=[CH:10][C:9]=1Br)(C)(C)C.[C:23]1(B(O)O)[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:15][NH:16][C:17](=[O:20])[NH:18][CH2:19]2)=[CH:10][C:9]=1[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 38629021-Cyclohexenylboronic acidHCID 59771302[2-Bromo-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester

생성물 1

HCID 597712825-(4-Amino-3-cyclohex-1-enyl-phenyl)-tetrahydro-pyrimidin-2-one

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물
촉매
HCID 6422Trifluoroacetic acid용매

실험 절차

[2-Bromo-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester (99 mg, 0.26 mmol, as prepared in the previous step) was dissolved in TFA (1 mL). The resulting mixture was stirred at RT for 30 min and concentrated in vacuo. The residue obtained was dried in vacuo for 1 h and diisolved in EtOH (0.5 mL) and toluene (1 mL). To this solution cyclohex-1-enyl boronic acid (20.5 mg, 0.16 mmol), 2M Na2CO3 (0.5 mL, 1 mmol) and Pd (PPh3)4 (30 mg, 0.025 mmol) were added. The resulting mixture was heated at 80° C. overnight. The reaction mixture was allowed to cool to RT and extracted with EtOAc (2×10 mL). The EtOAc layers were combined, dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified on silica (2% MeOH-EtOAc) to afford the title compound (31 mg) contaminated with Ph3PO, which was used in the next step without further purification: Mass spectrum (ESI, m/z): Calcd. for C16H21N3O, 272.1 (M+H). found 272.1.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. customwas dried in vacuo for 1 h
  4. temperatureThe resulting mixture was heated at 80° C. overnight
  5. temperatureto cool to RT
  6. extractionextracted with EtOAc (2×10 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue obtained
  10. customwas purified on silica (2% MeOH-EtOAc)

출처 및 근거

ORD 기록
ord-c7e2c0389fa642d3acc475c6de0fb821
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895584B2

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