Lithium Hexamethyldisilazide → (8-Cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester

HRID 586547

반응식

HRID 586547 반응식
C(O[C:4](=[O:18])[CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:29]1([NH:34][C:35]2[C:40]([CH:41]=O)=[CH:39][N:38]=[C:37]([S:43][CH3:44])[N:36]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1>O1CCCC1.C(OCC)(=O)C.O>[CH2:11]([O:10][C:8](=[O:9])[NH:7][CH2:6][C:5]1[C:4](=[O:18])[N:34]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:35]2[N:36]=[C:37]([S:43][CH3:44])[N:38]=[CH:39][C:40]=2[CH:41]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 107998964-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehydeHCID 12116647Ethyl 3-{[(benzyloxy)carbonyl]amino}propanoate

생성물 1

HCID 69208844(8-Cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

3-Benzyloxycarbonylamino-propionic acid ethyl ester (6.68 g, 26.58 mmol) was dissolved in tetrahydrofuran (40 mL) to which LiHMDS (28 mL, 28 mmol, 1.0 M in THF) was slowly added. 4-Cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (3.15 g, 13.29 mmol) was then added neat and the reaction mixture was 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 oil was purified by silica gel chromatography to give (8-cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester as pale yellow waxy solid (1.67 g, 29.6%). 1H NMR δ (400 MHz, CDCl3) 8.57 (s, 1H), 7.56 (s, 1H), 7.26-7.36 (m, 5H), 5.93 (m, 1H), 5.56 (t, J=6.1 Hz, 1H), 5.08 (s, 2H), 4.25 (d, J=6.2 Hz, 2H), 2.60 (s, 3H), 2.30 (m, 2H), 2.05 (m, 2H), 1.86 (m, 2H), 1.69 (m, 2H).

후처리

  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. customThe crude oil was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-be8670af070b48fba5f09e40a62fd5ec
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936612B2

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