4-Methylpyrimidine → HCID 136375617, 화합물

HRID 1296705

반응식

HRID 1296705 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12](OCC)=[O:13].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:8][C:9]1[CH:10]=[C:11]([C:12]([OH:13])=[CH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][N:3]=2)[CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 189224-MethylpyrimidineHCID 70785Ethyl 3-chlorobenzoateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 136375617HCID 136375617, 화합물수율 96.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cold (0° C.) solution of 4-methylpyrimidine (4.56 mL 50.1 mmol) and ethyl 3-chlorobenzoate (7.90 mL 50.1 mmol) in tetrahydrofuran (50 mL) was added lithium bis(trimethylsilyl)amide (100 mL, 1.0M in tetrahydrofuran, 100 mmol) dropwise over 30 minutes. The resultant mixture was warmed to room temperature and stirred 16 hours. The reaction mixture was concentrated in vacuo. The resultant oil was diluted with methanol. Upon standing, a solid precipitated, which was collected on a filter to provide 1-(3-chlorophenyl)-2-(4-pyrimidinyl)ethenol (11.2 g, 93%) as a yellow solid. Rf 0.31 (3:1 hexanes:ethyl acetate); 1H NMR (d6-DMSO) δ 8.37 (s, 1H), 7.98 (m, 1H), 7.81–7.76 (m, 2H), 7.38–7.32 (m, 2H), 6.71 (br, 1H), 5.65 (s, 1H); MS m/z 233 (M+1).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe resultant oil was diluted with methanol
  3. customa solid precipitated
  4. customwhich was collected on
  5. filtrationa filter

출처 및 근거

ORD 기록
ord-e771dfcbc4ea444089d4ba7654147751
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07247626B2

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