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Ethyl bromopyruvate → Ethyl 5-oxo-5,6-dihydroimidazo[1,2-c]pyrimidine-2-carboxylate

HRID 1409325
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HRID 1409325 반응식
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12]>C(O)C>[O:12]=[C:11]1[N:13]2[CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:15]=[C:14]2[CH:16]=[CH:17][NH:10]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 66144Ethyl bromopyruvateHCID 178418229Cytosine

생성물 1

HCID 136377293Ethyl 5-oxo-5,6-dihydroimidazo[1,2-c]pyrimidine-2-carboxylate수율 14.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ethyl bromopyruvate (18.00 mmol, 3.51 g) was dissolved in ethanol (50 ml). Cytosine (18.00 mmol, 2 g) was added and the resulting mixture was refluxed for 5.5 h. The mixture was evaporated and DCM was added. The precipitate was filtered and washed with water. The filtrate was washed with NaHCO3, water and evaporated. The evaporation residue and the previously filtered precipitate were purified by flash chromatography and trituration from water, respectively. 0.526 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.31 (t, 3H), 4.29 (q, 2H), 6.60 (d, 1H), 7.30-7.38 (m, 1H), 8.22 (s, 1H), 11.77 (bs, 1H).

후처리

  1. temperaturethe resulting mixture was refluxed for 5.5 h
  2. customThe mixture was evaporated
  3. additionDCM was added
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. washThe filtrate was washed with NaHCO3, water
  7. customevaporated
  8. customThe evaporation residue and the previously filtered precipitate were purified by flash chromatography and trituration from water

출처 및 근거

ORD 기록
ord-7021ecf3e231461e810bd2620090c4c8
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921378B2

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