4-Methoxybenzylamine → 4-chloro-7-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

HRID 1192425노트

반응식

HRID 1192425 반응식
Cl[C:2]1[C:7]([CH2:8][CH2:9]OS(C)(=O)=O)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>ClCCCl>[Cl:15][C:6]1[C:7]2[CH2:8][CH2:9][N:23]([CH2:22][C:21]3[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[C:2]=2[N:3]=[CH:4][N:5]=1

참가 물질

4

반응물 2

HCID 754524-MethoxybenzylamineHCID 86598737Methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester

생성물 1

HCID 529881474-chloro-7-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine수율 71%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester (0.50 g, 1.84 mmol) and 4-methoxybenzylamine (0.60 g, 4.37 mmol) in DCE (30 mL) and TEA (4 mL) was refluxed overnight. After cooling, the solvent was removed and the residue was subject to column chromatography, eluted by hexane/ethyl acetate (4:1) to give 4-Chloro-7-(4-methoxy-benzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (0.36 g, 71%). 1H NMR (CDCl3, 400 MHz) δ 8.35 (s, 1H), 7.26 (dd, J=2.8 Hz, J=1.6 Hz, 2H), 6.88 (d, J=4.4 Hz, 2H), 5.33 (s, 1H), 4.62 (d, J=5.6 Hz, 2H), 3.81 (s, 3H), 3.73 (t, J=7.2 Hz, 2H), 3.04 (t, J=6.8 Hz, 2H). MS (APCI+) [M+H]+276.

후처리

  1. temperatureAfter cooling
  2. customthe solvent was removed
  3. washeluted by hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-72c4bdf021f74e1fbd53b37ac7d7140e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680114B2

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