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

HRID 2207708ノート

反応式

HRID 2207708 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-0b29956c3a2a4e19854f56dbdb02ba42
出典データセット
uspto-grants-2016_06
特許番号
US09376448B2

反応ノート

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