Water → 3-{[(2-{[3-(2-Bromoethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol

HRID 1614932ノート

反応式

HRID 1614932 の反応式
[Cl:1][C:2]1[C:3]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16]O)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.ClCCl.B(Br)(Br)[Br:32].O>CCOC(C)=O>[Br:32][CH2:16][CH2:15][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:18][CH2:19][C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)[CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 962WaterHCID 6344Dichloromethane2 回HCID 25134Boron tribromideHCID 584679152-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]ethanol

生成物 1

HCID 584678993-{[(2-{[3-(2-Bromoethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol収率 20%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Into a 1-neck round-bottom flask were added 2-[3-({5-chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]ethanol (0.20 g, 0.52 mmol) and dichloromethane (“DCM”, 5 mL). To the reaction mixture was added a solution of boron tribromide in methylene chloride (1.6 mL, 1.6 mmol, 1.0 M) at 0° C. The resulting mixture was allowed to warm up to rt and stirred overnight. The resulted mixture was cooled in a dry ice bath when water (10 mL) was added. The mixture was allowed to warm up to rt and EtOAc was added. The aqueous layer was extracted with EtOAc twice. The organic layers were combined and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product as a light brown powder (34 mg, 20%). LCMS for C19H19BrClN4O (M+H)+: m/z=371.1, 373.1. 1H NMR (400 MHz, DMSO-d6): δ 9.30 (s, 1H), 9.11 (s, 1H), 7.95 (s, 1H), 7.74 (t, J=6.1 Hz, 1H), 7.42 (m, 1H), 7.08 (t, J=7.9 Hz, 1H), 7.03 (dd, J=8.7, 7.6 Hz, 1H), 6.71 (dd, J=11.5, 7.6 Hz, 1H), 6.69 (s, 1H), 6.58 (dd, J=8.0, 2.3 Hz, 1H), 4.56 (m, 2H), 3.50 (m, 2H), 2.56 (t, J=7.1 Hz, 2H).

後処理

  1. additionwas added
  2. temperatureto warm up to rt
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-135f6381a168424b9dd6539a1db09d15
出典データセット
uspto-grants-2014_07
特許番号
US08765727B2

反応ノート

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