1,4-Dioxane → (1R)-2-{[2-Cyclopropyl-6-(3,4-dichlorophenyl)pyrimidin-4-yl]amino}-1-phenylethanol

HRID 1908249ノート

反応式

HRID 1908249 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[C:4]([CH:16]2[CH2:18][CH2:17]2)[N:3]=1.[NH2:19][CH2:20][C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22].C([O-])(O)=O.[Na+].O1CCOCC1>O>[CH:16]1([C:4]2[N:3]=[C:2]([NH:19][CH2:20][C@@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[OH:22])[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=3)[N:5]=2)[CH2:18][CH2:17]1

参加物

6

反応物 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 6951165(R)-(-)-2-Amino-1-phenylethanolHCID 809526634-Chloro-2-cyclopropyl-6-(3,4-dichloro-phenyl)-Pyrimidine

生成物 1

HCID 44205060(1R)-2-{[2-Cyclopropyl-6-(3,4-dichlorophenyl)pyrimidin-4-yl]amino}-1-phenylethanol収率 82%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 4-chloro-2-cyclopropyl-6-(3,4-dichloro-phenyl)-pyrimidine (108 mg, 0.364 mmol), (R)-(−)-2-amino-1-phenylethanol (67.2 mg, 0.490 mmol), and NaHCO3 (190.1 mg, 2.26 mmol) and 1,4-dioxane was refluxed for 48 h. The mixture was poured into water and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated. The crude residue was purified (FCC) to give the title compound as a white solid (119.4 mg, 82%). MS (ESI): mass calcd. for C21H19Cl2N3O, 399.09; m/z found, 400.1 [M+H]+. 1H NMR (CD3OD): 8.13-8.05 (m, 1H), 7.85-7.79 (m, 1H), 7.64-7.58 (m, 1H), 7.45-7.31 (m, 4H), 7.30-7.23 (m, 1H), 6.68-6.59 (m, 1H), 4.93-4.85 (m, 1H), 3.81-3.65 (m, 1H), 3.56-3.48 (m, 1H), 2.16-2.01 (m, 1H), 1.16-1.09 (m, 2H), 1.02-0.94 (m, 2H).

後処理

  1. temperaturewas refluxed for 48 h
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC)

出典と根拠

ORDレコード
ord-65d87a4bc51344aea22e753149c83c2f
出典データセット
uspto-grants-2013_12
特許番号
US08598202B2

反応ノート

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