Trifluoroacetic acid → 2-(4-(4-(4-(2-Aminopropan-2-yl)phenyl)-5-chloropyrimidin-2-ylamino)phenyl)ethanol

HRID 1359448

反応式

HRID 1359448 の反応式
C(OC([NH:8][C:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20](Cl)[N:19]=2)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])=O)(C)(C)C.[NH2:26][C:27]1[CH:35]=[CH:34][C:30]([CH2:31][CH2:32][OH:33])=[CH:29][CH:28]=1.FC(F)(F)C(O)=O>C(OCCO)C>[NH2:8][C:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([NH:26][C:27]3[CH:35]=[CH:34][C:30]([CH2:31][CH2:32][OH:33])=[CH:29][CH:28]=3)[N:19]=2)=[CH:16][CH:17]=1)([CH3:10])[CH3:11]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 669044-Aminophenethyl alcoholHCID 181832304-[4-(1-Tert-butoxycarbonylamino-1-methylethyl)phenyl]-2,5-dichloropyrimidine

生成物 1

HCID 99080262-(4-(4-(4-(2-Aminopropan-2-yl)phenyl)-5-chloropyrimidin-2-ylamino)phenyl)ethanol

試薬・触媒・溶媒 1

HCID 8076Glycol monoethyl ether溶媒

実験手順

A mixture of 4-[4-(1-tertbutoxycarbonylamino-1-methylethyl)phenyl]-2,5-dichloropyrimidine (1.53 g, 4.0 mmol) and 4-aminophenethyl alcohol (1.10 g, 8.0 mmol) in 2-ethoxyethanol (15 ml) was heated to reflux for 18 h. The reaction was cooled to room temperature, trifluoroacetic acid (2 ml) added and the reaction stirred for 30 min. Solvent was removed in vacuo and the residue partitioned between CH2Cl2 (100 ml) and saturated, aqueous Na2CO3 (80 ml). The aqueous layer was re-extracted with CH2Cl2 (2×80 ml) and the combined CH2Cl2 layer washed with aqueous Na2CO3 (80 ml), brine (80 ml), dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica, 10-15% methanol in CH2Cl2) to give the title compound as a buff solid (1.30 g) m.p. 162-163°. δH (d6DMSO) 9.74 (1H, s), 8.55 (1H, s), 7.76 (2H, d, J 8.5 Hz), 7.68 (2H, d, J 8.5 Hz), 7.62 (2H, d, J 8.5 Hz), 7.12 (2H, d, J 8.5 Hz), 4.57 (1H, bs), 3.55 (2H, m), 2.65 (2H, t, J 7.2 Hz), 1.41 (6H, s); MS (ESI) 383 (MH+, 35Cl, 100%).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. customSolvent was removed in vacuo
  4. customthe residue partitioned between CH2Cl2 (100 ml)
  5. extractionThe aqueous layer was re-extracted with CH2Cl2 (2×80 ml)
  6. washthe combined CH2Cl2 layer washed with aqueous Na2CO3 (80 ml), brine (80 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (silica, 10-15% methanol in CH2Cl2)

出典と根拠

ORDレコード
ord-8e969767587e4fc185332acaf09ac5a9
出典データセット
uspto-grants-2003_07
特許番号
US06600037B1

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