Ethyl Acetate → 4-Chloro-6-(4-cyclobutylpiperazin-1-yl)pyrimidine

HRID 2039474ノート

反応式

HRID 2039474 の反応式
Cl.Cl.[CH:3]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4]1.C(N(C(C)C)C(C)C)C.[Cl:22][C:23]1[CH:28]=[C:27](Cl)[N:26]=[CH:25][N:24]=1.C(OCC)(=O)C>O>[Cl:22][C:23]1[CH:28]=[C:27]([N:10]2[CH2:11][CH2:12][N:7]([CH:3]3[CH2:6][CH2:5][CH2:4]3)[CH2:8][CH2:9]2)[N:26]=[CH:25][N:24]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 451567991-Cyclobutylpiperazine dihydrochloride

生成物 1

HCID 579250694-Chloro-6-(4-cyclobutylpiperazin-1-yl)pyrimidine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

1.8 g (8.4 mmol) of 1-cyclobutylpiperazine dihydrochloride (Zaragoza et al., J. Med. Chem. 2004, 47, 2833) are initially charged in 18 ml of water, and 2.9 ml (2.1 g, 16.9 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine are added. The mixture is stirred at RT for 30 min, and 1.3 g (8.4 mmol) of 4,6-dichloropyrimidine are added. The reaction mixture is stirred at 115° C. for 1 h and cooled to RT, 25 ml of ethyl acetate are added and the mixture is extracted with 25 ml of a saturated aqueous sodium bicarbonate solution. The organic phase is separated off, dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100/3). Yield: 1.9 g (89% of theory)

後処理

  1. stirringThe reaction mixture is stirred at 115° C. for 1 h
  2. temperaturecooled to RT
  3. extractionthe mixture is extracted with 25 ml of a saturated aqueous sodium bicarbonate solution
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100/3)

出典と根拠

ORDレコード
ord-2545bbcfed6d4309aa083379f94461a5
出典データセット
uspto-grants-2013_11
特許番号
US08580778B2

反応ノート

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