Diglyme → 6-(2-Fluoro-4-nitrophenoxy)-N-(4-methoxybenzyl)pyrimidin-4-amine

HRID 1670201ノート

反応式

HRID 1670201 の反応式
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13](Cl)[N:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[F:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[OH:28].CCN(C(C)C)C(C)C.COCCOCCOC>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([O:28][C:20]3[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=3[F:18])[N:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 8150DiglymeHCID 98252-Fluoro-4-nitrophenolHCID 81531DiisopropylethylamineHCID 223094976-Chloro-N-(4-methoxybenzyl)pyrimidin-4-amine

生成物 1

HCID 593016056-(2-Fluoro-4-nitrophenoxy)-N-(4-methoxybenzyl)pyrimidin-4-amine収率 76%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
160 °C

実験手順

A mixture of N-(4-methoxybenzyl)-6-chloropyrimidin-4-amine (2.3 g, 9.2 mmol), 2-fluoro-4-nitrophenol (1.45 g, 9.2 mmol), DIPEA (15 mL), and 2-methoxyethyl ether (75 mL) was heated at 160° C. in a sealed pressure bottle for 50 h. The mixture was cooled, poured onto crushed ice (200 g), treated with EtOAc (200 mL). After vigorously stirring for 10 min, the insoluble material was filtered off. The EtOAc phase was washed with saturated aq. Na2CO3 solution (100 mL), brine (3×100 mL), dried (MgSO4) and concentrated in vacuo. The gummy solid obtained was triturated with isopropyl ether to give the title compound (1.75 g, 76%) as a brown solid. 1H NMR (DMSO-d6) δ 8.32 (dd, 1H, J=10.2, 2.0 Hz), 8.15 (d, 2H, J=9.2 Hz), 8.05 (br s, 1H), 7.61 (dd, 1H, J=8.4, 8.4 Hz), 7.26 (d, 2H, J=8.5 Hz), 6.91 (d, 2H, J=8.5 Hz), 6.14 (br s, 1H), 4.48 (br s, 2H), 3.74 (s, 3H).

後処理

  1. temperatureThe mixture was cooled
  2. additionpoured
  3. filtrationthe insoluble material was filtered off
  4. washThe EtOAc phase was washed with saturated aq. Na2CO3 solution (100 mL), brine (3×100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe gummy solid obtained
  8. customwas triturated with isopropyl ether

出典と根拠

ORDレコード
ord-76156b78f019425687d74faf0b5a72eb
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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