4,6-Dichloropyrimidine → 6-chloro-N-(2-(2-methoxyphenyl)propyl)pyrimidin-4-amine

HRID 929537노트

반응식

HRID 929537 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]([CH3:20])[CH2:18][NH2:19].CCN(C(C)C)C(C)C>C(O)(C)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:19][CH2:18][CH:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])[CH3:20])[CH:7]=1

참가 물질

5

반응물 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 4080602-(2-Methoxyphenyl)propan-1-amine

생성물 1

HCID 866996526-chloro-N-(2-(2-methoxyphenyl)propyl)pyrimidin-4-amine수율 77%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

As shown in step 4-v of Scheme 4, a mixture of 4,6-dichloropyrimidine (817 mg, 5.49 mmol), 2-(2-methoxyphenyl)-1-propanamine (0.997 g, 6.03 mmol), and DIEA (2.13 g, 2.87 mL, 16.5 mmol) in isopropanol (5.0 mL) was stirred for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue purified by medium pressure chromatography on silica gel (25% EtOAc in hexanes) to give 6-chloro-N-(2-(2-methoxyphenyl)propyl)pyrimidin-4-amine as a colorless solid (Compound 2012, 1.18 g, 77% yield): 1H NMR (CDCl3) δ 8.31 (s, 1H), 7.23 (dd, J=12.0, 4.5 Hz, 2H), 7.03-6.87 (m, 2H), 6.41 (s, 1H), 5.42 (s, 1H), 3.89 (s, 3H), 3.67-3.18 (m, 3H), 1.35 (d, J=6.8 Hz, 3H).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by medium pressure chromatography on silica gel (25% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-fdf14f5b47f14d42a8d27dac4b0cc750
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296701B2

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