Ethyl 3-ethoxypropionate → 8-cyclopentyl-6-ethoxymethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 272503

反応式

HRID 272503 の反応式
C(O[C:4](=[O:10])[CH2:5][CH2:6][O:7][CH2:8][CH3:9])C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:21]1([NH:26][C:27]2[C:32]([CH:33]=O)=[CH:31][N:30]=[C:29]([S:35][CH3:36])[N:28]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1>O1CCCC1.C(OCC)(=O)C.O>[CH:21]1([N:26]2[C:27]3[N:28]=[C:29]([S:35][CH3:36])[N:30]=[CH:31][C:32]=3[CH:33]=[C:5]([CH2:6][O:7][CH2:8][CH3:9])[C:4]2=[O:10])[CH2:22][CH2:23][CH2:24][CH2:25]1

参加物

7

反応物 3

HCID 12989Ethyl 3-ethoxypropionateHCID 2733832Lithium HexamethyldisilazideHCID 107998964-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

生成物 1

HCID 113016288-cyclopentyl-6-ethoxymethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one収率 34.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

3-Ethoxy-propionic acid ethyl ester (12.31 g, 84.2 mmol) was dissolved in tetrahydrofuran (40 mL) to which LiHMDS (89 mL, 88.9 mmol, 1.0 M in THF) was slowly added. 4-Cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (10.0 g, 42.2 mmol) was then added neat and the reaction mixture was stirred at ambient temperature for 17 hours then brought to reflux for 7 hours. The reaction mixture was diluted with ethyl acetate and water, the layers separated, the organic layer dried over MgSO4 and the solvent evaporated to give a crude oil. The crude product was dissolved in ethyl acetate and diluted with hexanes to give a precipitate, which was collected by filtration to give 8-cyclopentyl-6-ethoxymethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as an off-white solid (4.70 g, 34.9%).1H NMR δ(400 MHz, CDCl3) 8.47 (s, 1H), 7.52 (t, J=1.5 Hz, 1H), 5.82 (m, 1H), 4.32 (d, J=1.7 Hz, 1H), 3.53 (q, J=7.1 Hz, 2H), 2.47 (s, 3H), 2.17 (m, 2H), 1.93 (m, 2H), 1.73 (m, 2H), 1.54 (m, 2H), 1.15 (t, J=7.1 Hz, 3H).

後処理

  1. additionwas slowly added
  2. temperatureto reflux for 7 hours
  3. customthe layers separated
  4. dry with materialthe organic layer dried over MgSO4
  5. customthe solvent evaporated
  6. customto give a crude oil
  7. customto give a precipitate, which
  8. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-071b2cbccc324cd58a90337a8fcc77fb
出典データセット
uspto-grants-2008_11
特許番号
US07456168B2

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