Methyl 3-methoxypropionate → 8-cyclopentyl-6-methoxymethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 586538노트

반응식

HRID 586538 반응식
CO[C:3](=[O:8])[CH2:4][CH2:5][O:6][CH3:7].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:19]1([NH:24][C:25]2[C:30]([CH:31]=O)=[CH:29][N:28]=[C:27]([S:33][CH3:34])[N:26]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCCC1.C(OCC)(=O)C.O>[CH:19]1([N:24]2[C:25]3[N:26]=[C:27]([S:33][CH3:34])[N:28]=[CH:29][C:30]=3[CH:31]=[C:4]([CH2:5][O:6][CH3:7])[C:3]2=[O:8])[CH2:20][CH2:21][CH2:22][CH2:23]1

참가 물질

7

반응물 3

HCID 19710Methyl 3-methoxypropionateHCID 2733832Lithium HexamethyldisilazideHCID 107998964-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

생성물 1

HCID 114381748-cyclopentyl-6-methoxymethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one수율 24.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

3-Methoxy-propionic acid methyl ester (9.95 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 brought to reflux for 7 days. 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-methoxymethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as an off-white solid (3.11 g, 24.1%). 1H NMR δ (400 MHz, CDCl3) 8.46 (s, 1H), 7.49 (t, J=1.7 Hz, 1H), 5.81 (m, 1H), 4.28 (d, J=1.7 Hz, 1H), 3.37 (s, 3H), 2.47 (s, 3H), 2.18 (m, 2H), 1.93 (m, 2H), 1.73 (m, 2H), 1.55 (m, 2H).

후처리

  1. additionwas slowly added
  2. temperatureto reflux for 7 days
  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

출처 및 근거

ORD 기록
ord-2efc94e5780342d78bd0943f6f704ec4
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936612B2

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