2-Chloro-5-nitropyrimidine → HCID 53260086, 화합물

HRID 508653

반응식

HRID 508653 반응식
[C:1]12([C:11]3[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl[C:29]1[N:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][N:30]=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.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>[C:1]12([C:11]3[CH:12]=[C:13]([C:29]4[N:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][N:30]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

참가 물질

6

반응물 3

HCID 825442-Chloro-5-nitropyrimidineHCID 516892Sodium BicarbonateHCID 12134904HCID 12134904, 화합물

생성물 1

HCID 53260086HCID 53260086, 화합물수율 19%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

To a solution of 3-(1-adamantyl)-4-benzyloxyphenylboronic acid (1) (833 g, 2.3 mmol) and 2-chloro-5-nitropyrimidine (2) (320 mg, 2.00 mmol) in degassed toluene (15 mL) was added tetrakis(triphenylphosphine)palladium (347 mg, 0.300 mmol), NaHCO3 (336 mg, 4.00 mmol) and degassed H2O (3 mL). The mixture was heated at reflux (90° C. oil-bath) for 24 h, cooled to room temperature and extracted with EtOAc (180 mL). The extract was washed (H2O and brine) and dried. After solvent removal at reduced pressure, the residue was chromatographed (3% EtOAc/hexane) to give 165 mg (19%) of 2-[3-(1-adamantyl)-4-benzyloxyphenyl]-5-nitropyrimidine as a yellow solid, mp 206° C. (dec). IR 2902, 1405, 1179 cm−1; 1H NMR (CDCl3) δ 1.76 (bs, 6H, AdCH2), 2.09 (bs, 311, AdCH), 2.22 (m, 6H, AdCH2), 5.24 (s, 2H, C6H5CH2), 7.07 (d, J=8.7 Hz, 1H, 5′-ArH), 7.34-7.53 (m, 5H, C6H5), 8.40 (dd, J=8.7 Hz, 2.4 Hz, 1H, 6′-ArH), 8.51 (d, J=2.4 Hz, 1H, 2′-ArH), 9.46 ppm (s, 2H, 4-ArH, 6-ArH). HRMS calcd C27H27N3O3 [M+H]+ 442.2125. found 442.2137.

후처리

  1. customdegassed H2O (3 mL)
  2. temperatureThe mixture was heated
  3. temperaturecooled to room temperature
  4. extractionextracted with EtOAc (180 mL)
  5. washThe extract was washed (H2O and brine)
  6. customdried
  7. customAfter solvent removal at reduced pressure
  8. customthe residue was chromatographed (3% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-ff0bd70eb6a4423f90afdcec38042ca9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096544B2

연결된 노트

불러오는 중…