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

HRID 28629

반응식

HRID 28629 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-83dda32384ec47fbba0a02bb6e16db17
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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