Diisopropylethylamine → 6-[4-(2-chloro-6-fluorobenzyl)-piperazin-1-yl]-3H-pyrimidin-4-one

HRID 1993436

反応式

HRID 1993436 の反応式
[N:1]1([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:16]=1[CH2:17]N1CCNCC1.C(N(C(C)C)CC)(C)C>CC(O)CC>[Cl:14][C:15]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:16]=1[CH2:17][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:2][CH2:3]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 7357371-((2-Chloro-6-fluorophenyl)methyl)piperazineHCID 1361025406-piperazin-1-yl-3H-pyrimidin-4-one2 回

生成物 1

HCID 1363463246-[4-(2-chloro-6-fluorobenzyl)-piperazin-1-yl]-3H-pyrimidin-4-one収率 17.1%

試薬・触媒・溶媒 1

HCID 6568(+-)-2-Butanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-chloro-3H-pyrimidin-4-one (Intermediate 4; 100 mg, 0.77 mmol), 1-(2-chloro-6-fluorobenzyl)piperazine (Oakwood; 87 mg, 0.38 mmol), and diisopropylethylamine (200 μL, 1.1 mmol) in 2-butanol (5 mL) was heated in a sealed scintillation vial on a hot plate at about 80° C. for 8 hours and then allowed to cool to room temperature and stand at room temperature for 40 hours. The mixture was filtered. The solid was washed with 2-butanol and air-dried to give 6-[4-(2-chloro-6-fluorobenzyl)-piperazin-1-yl]-3H-pyrimidin-4-one (21 mg, 17%) as a white solid, mp 255-256° C. (dec). 1H NMR (d6-DMSO) δ 2.41-2.44 (m, 4H), 3.42-3.45 (m, 4H), 5.24 (s, 1H), 7.19-7.24 (m, 1H), 7.40-7.43 (m, 1H), 7.51-7.56 (m, 1H), 7.87 (s, 1H), 11.61 (br s, 1H). LRMS ES+M+H 323. HRMS Calcd. for C15H17ClFN4O (M+H), 323.1070. Found, 323.1069.

後処理

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was filtered
  3. washThe solid was washed with 2-butanol
  4. customair-dried

出典と根拠

ORDレコード
ord-f582eb83ccd54459ac142b854cdaf405
出典データセット
uspto-grants-2010_01
特許番号
US07652013B2

関連ノート

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