2-Chloro-5-nitropyrimidine → HCID 53260086、化合物

HRID 508653

反応式

HRID 508653 の反応式
[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

参加物

6

反応物 3

HCID 825442-Chloro-5-nitropyrimidineHCID 516892Sodium BicarbonateHCID 12134904HCID 12134904、化合物

生成物 1

HCID 53260086HCID 53260086、化合物収率 19%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ff0bd70eb6a4423f90afdcec38042ca9
出典データセット
uspto-grants-2015_08
特許番号
US09096544B2

関連ノート

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