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N-methyl-2-pyrrolidone → Methyl 2-((2-chloropyrimidin-4-yl)amino)-2-methylbutanoate

HRID 1529252
ノート
印刷プレビュー

反応式

HRID 1529252 の反応式
[NH2:1][C:2]([CH3:9])([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].[Cl:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[CH:13][N:12]=1.CN1C(=O)CCC1>O>[Cl:10][C:11]1[N:16]=[C:15]([NH:1][C:2]([CH3:9])([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4])[CH:14]=[CH:13][N:12]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 775312,4-DichloropyrimidineHCID 4715131Methyl 2-amino-2-methylbutanoate

生成物 1

HCID 86682097Methyl 2-((2-chloropyrimidin-4-yl)amino)-2-methylbutanoate収率 98.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A 250 mL flask was charged with methyl 2-amino-2-methylbutanoate (8.4 g, 54.4 mmol), 2,4-dichloropyrimidine (8.9 g, 59.8 mmol), TEA(5.5 g, 54.4 mmol) and 80 mL NMP. The reaction mixture was heated to 80° C. for ˜18 hours. After cooling, water (300 mL) was added and the mixture extracted with MTBE. The organic extracts were washed with water and dried over sodium sulfate. Filtration and evaporation under vacuum afforded 13 g of an orange oil which was purified by flash chromatography, (0-100% ethyl acetate-hexane affording 4.6 g (34%) methyl 2-((2-chloropyrimidin-4-yl)amino)-2-methylbutanoate as an oil. 1H NMR: (CDCl3) δ 8.05-7.88 (m, 1H), 6.28 (δ, 1H), 5.95 (δ, 1H), 4.2-4.0 (μ, 1H), 3.86 (m, 1H), 2.46 (m, 1H), 2.10 (m, 1H), 2.01 (m, 1H), 1.72 (m, 3H), 0.89 (m, 3H). m/e, m+1 244.1

後処理

  1. temperatureAfter cooling
  2. extractionthe mixture extracted with MTBE
  3. washThe organic extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and evaporation under vacuum

出典と根拠

ORDレコード
ord-a79cd702280245248985830ced4a84be
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090614B2

反応ノート

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