4,6-Dichloropyrimidine → 6-Chloro-N-(4-methoxybenzyl)pyrimidin-4-amine

HRID 1670200ノート

反応式

HRID 1670200 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:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>CCCCO>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:16][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 709434,6-DichloropyrimidineHCID 754524-MethoxybenzylamineHCID 81531Diisopropylethylamine

生成物 1

HCID 223094976-Chloro-N-(4-methoxybenzyl)pyrimidin-4-amine収率 91.5%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

A mixture of 4,6-dichloropyrimidine (Aldrich, 3.6 g, 24.2 mmol), 4-methoxybenzylamine (2.7 g, 19.7 mmol), DIPEA (5 ml, 28.8 mmol), and n-BuOH was heated at reflux for 3 h. The mixture was concentrated and the residue treated with H2O (150 mL) and EtOAc (175 mL). The EtOAc phase was separated, washed with saturated aq. NaHCO3 solution and brine, dried (MgSO4), and concentrated to give the title compound (4.5 g) which was used without further purification. 1H NMR (DMSO-d6) δ 8.29 (s, 1H), 8.13 (br s, 1H), 7.25 (d, 2H, J=8.2 Hz), 6.90 (d, 2H, J=8.2 Hz), 6.56 (s, 1H), 4.48 (s, 2H), 3.75 (s, 3H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. additionthe residue treated with H2O (150 mL) and EtOAc (175 mL)
  5. customThe EtOAc phase was separated
  6. washwashed with saturated aq. NaHCO3 solution and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c9f511c726e84762a8da465178fa87c3
出典データセット
uspto-grants-2011_08
特許番号
US07989477B2

反応ノート

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