1-Propanol → 4-(5-Bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine

HRID 28629ノート

反応式

HRID 28629 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=2[OH:15])[CH:5]=[C:4]([Cl:16])[N:3]=1.[CH2:17](O)[CH2:18][CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:17][CH2:18][CH3:19])=[C:8]([C:6]2[CH:5]=[C:4]([Cl:16])[N:3]=[C:2]([NH2:1])[N:7]=2)[CH:13]=1

参加物

6

反応物 4

HCID 10311-PropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1360800122-(2-Amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol

生成物 1

HCID 860043744-(5-Bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine収率 52.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the stirred solution of 2-(2-amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol (0.060 g, 0.20 mmol), 1-propanol (0.036 g, 0.60 mmol), and triphenylphosphine (0.157 g, 0.60 mmol) in tetrahydrofuran (5.0 ml) was added diethyl azodicarboxylate (0.104 g, 0.60 mmol). After stirring for 16 hours, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:6) to provide 4-(5-bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine (0.036 g, 52% yield) as a white powder.

後処理

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:6)

出典と根拠

ORDレコード
ord-83dda32384ec47fbba0a02bb6e16db17
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

反応ノート

読み込み中…