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Sodium Carbonate → 3-{2-[(2-{[3-(3-Bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

HRID 1614962
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HRID 1614962 반응식
[Cl:1][C:2]1[C:3]([NH:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28]C)[CH:23]=2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17]O)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.B(Br)(Br)[Br:31].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C(=O)=O>[Br:31][CH2:17][CH2:16][CH2:15][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:19][CH2:20][CH2:21][C:22]3[CH:23]=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)[CH:14]=[CH:13][CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 584679083-{3-[(5-Chloro-4-{[2-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}propan-1-ol

생성물 1

HCID 584678483-{2-[(2-{[3-(3-Bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol수율 96%

시약·촉매·용매 2

HCID 280Carbon Dioxide용매
HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 3-{3-[(5-chloro-4-{[2-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}propan-1-ol (0.41 g, 0.73 mmol) in methylene chloride (4.7 mL) was added slowly a solution of boron tribromide in methylene chloride (3.6 mL, 3.6 mmol, 1.0 M) at 0° C. The mixture was allowed to warm up to rt and stirred overnight. The resultant mixture was cooled in dry ice when Na2CO3 (saturated aqueous solution) was added. The mixture was filtered and the solid collected was triturated with EtOAc, followed by washing with EtOAc and water successively to give the desired product as an off-white powder (322 mg, 96%). LCMS for C21H23BrClN4O (M+H)+: m/z=461.0, 463.0. 1H NMR (400 MHz, CD3OD): δ 7.96 (s, 1H), 7.92 (s, 1H), 7.37 (m, 3H), 7.16 (t, J=7.2 Hz, 1H), 6.94 (m, 1H), 6.62 (m, 2H), 3.75 (t, J=7.6 Hz, 2H), 3.43 (t, J=6.8 Hz, 2H), 2.84 (t, J=8.0 Hz, 2H), 2.76 (t, J=8.0 Hz, 2H), 2.15 (m, 2H).

후처리

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customthe solid collected
  4. customwas triturated with EtOAc
  5. washby washing with EtOAc and water successively

출처 및 근거

ORD 기록
ord-847dbd4ce3f749d2b75bc18da03f0a52
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765727B2

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