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

HRID 1529252
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HRID 1529252 반응식
[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
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5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
80 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-a79cd702280245248985830ced4a84be
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090614B2

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