Lawesson's reagent → 3-(Benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carbothioamide

HRID 390335노트

반응식

HRID 390335 반응식
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH2:24])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1COCC1>[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22](=[S:34])[NH2:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 584589253-(Benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide

생성물 1

HCID 584589233-(Benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carbothioamide수율 82.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a solution of 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide (0.54 g, 1.64 mmol, 1.0 equiv) in THF (33 mL) under a nitrogen atmosphere, was added Lawesson's reagent (0.40 g, 0.98 mmol, 0.6 equiv). The yellow solution was then heated to 70° C. (oil bath). After stirring for 1 h, the reaction was cooled to ambient temperature and concentrated in vacuo. The crude product was purified by silica gel chromatography (30-100% ethyl acetate/hexane) to provide the title compound (0.28 g, 49% yield) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.04 (s, 1H), 7.63 (s, 1H), 7.50-7.57 (m, 2H), 7.27-7.41 (m, 3H), 5.30 (s, 2H), 3.96-4.08 (m, 4H), 1.62 (s, 6H); LCMS (ES+, (M+H)+) m/z 346.17.

후처리

  1. temperaturethe reaction was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by silica gel chromatography (30-100% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-925b465a6c284fa7831915e848c9dd12
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383639B2

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