Ethyl 2-(benzyloxy)-3-oxopropanoate → HCID 178517543, 화합물

HRID 1774433

반응식

HRID 1774433 반응식
[CH2:1]([O:8][CH:9]([CH:15]=O)[C:10]([O:12]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[C:22]([C:24](=[NH:26])[NH2:25])[CH:21]=[CH:20][N:19]=1>C(O)C>[CH2:1]([O:8][C:9]1[C:10]([OH:12])=[N:25][C:24]([C:22]2[CH:21]=[CH:20][N:19]=[C:18]([Cl:17])[CH:23]=2)=[N:26][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 19903223Ethyl 2-(benzyloxy)-3-oxopropanoateHCID 509886352-Chloropyridine-4-carboximidamide

생성물 1

HCID 178517543HCID 178517543, 화합물수율 66%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of crude ethyl 2-(benzyloxy)-3-oxopropanoate (all from previous step), 2-chloropyridine-4-carboximidamide (9.57 g, 50 mmol) and 100 mL of anhydrous ethanol was refluxed for 4 h under nitrogen. The mixture was then cooled and the volatile solvents were removed by rotary-evaporator. The residue was re-dissolved in water and filtered. The filtrate was acidified by HCl (4N aq) in an ice bath and the white precipitate was filtered, washed with water, and dried to give 5-(benzyloxy)-2-(2-chloropyridin-4-yl)pyrimidin-4-ol (10.4 g, 66%). 1H NMR δ (400 MHz, d6-DMSO): 13.12 (s, 1H), 8.58 (d, J=5.2 Hz, 1H), 8.12 (s, 1H), 8.04 (d, J=5.2 Hz, 1H), 7.94 (s, 1H), 7.51-7.34 (m, 5H), 5.20 (s, 2H); MS (ESI) m/z (M++H)+ 314.

후처리

  1. temperaturewas refluxed for 4 h under nitrogen
  2. temperatureThe mixture was then cooled
  3. customthe volatile solvents were removed by rotary-evaporator
  4. dissolutionThe residue was re-dissolved in water
  5. filtrationfiltered
  6. customThe filtrate was acidified by HCl (4N aq) in an ice bath
  7. filtrationthe white precipitate was filtered
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-c8e27d6be1ba40568755340dbf21efba
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260413B2

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