Sodium hydride → HCID 90416929, 화합물

HRID 57341

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HRID 57341 반응식
[F:1][C:2]([F:12])([F:11])[CH:3]([CH:5]1[CH2:9][O:8][C:7](=[O:10])[NH:6]1)[CH3:4].[F:13][C:14]1[N:19]=[C:18](F)[CH:17]=[CH:16][N:15]=1.[H-].[Na+]>CN(C=O)C>[F:13][C:14]1[N:19]=[C:18]([N:6]2[CH:5]([CH:3]([CH3:4])[C:2]([F:1])([F:11])[F:12])[CH2:9][O:8][C:7]2=[O:10])[CH:17]=[CH:16][N:15]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 1377162,4-DifluoropyrimidineHCID 904145974-(1,1,1-Trifluoropropan-2-yl)oxazolidin-2-one

생성물 1

HCID 90416929HCID 90416929, 화합물수율 24.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A solution of 4-(1,1,1-trifluoropropan-2-yl)oxazolidin-2-one (270 mg, 1.474 mmol) and 2,4-difluoropyrimidine (171 mg, 1.474 mmol, 1 eq) in DMF (4 mL) was treated with NaH (60%, 88 mg, 2.212 mmol, 1.5 eq), then the resulting mixture was stirred at 0° C. for 10 minutes, then room temperature for 1 h. The reaction mixture was quenched with sat. Na2SO4 (15 mL) diluted with EtOAc (20 mL), washed and 4% aqueous NaCl (3×20 mL), dried over Na2SO4, concentrated in vacuo. Flash column chromatography (silica, 120 g, 15 m) 5% EtOAc/DCM to provide 3-(2-fluoropyrimidin-4-yl)-4-(1,1,1-trifluoropropan-2-yl)oxazolidin-2-one (100 mg, white solid). 1H NMR (400 MHz, CDCl3) δ 8.55 (dd, J=5.8, 2.1 Hz, 1H), 8.20 (dd, J=5.8, 3.7 Hz, 1H), 5.04-4.84 (m, 1H), 4.68 (dd, J=9.5, 2.6 Hz, 1H), 4.54 (t, J=9.2 Hz, 1H), 3.34 (ddddd, J=13.3, 9.3, 7.1, 3.9, 1.6 Hz, 1H), 1.29 (d, J=7.3 Hz, 3H). MS 279.0631 m/z.

후처리

  1. waitroom temperature for 1 h
  2. customThe reaction mixture was quenched with sat. Na2SO4 (15 mL)
  3. additiondiluted with EtOAc (20 mL)
  4. washwashed
  5. dry with material4% aqueous NaCl (3×20 mL), dried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-683c70c0d6c4446491f968ad54a4e1af
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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