Sodium hydride → HCID 86730137, 화합물

HRID 1850108노트

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HRID 1850108 반응식
[F:1][C:2]1[N:7]=[C:6](F)[CH:5]=[CH:4][N:3]=1.[CH:9]([C@H:12]1[CH2:16][O:15][C:14](=[O:17])[NH:13]1)([CH3:11])[CH3:10].[H-].[Na+]>CN(C=O)C.O>[F:1][C:2]1[N:7]=[C:6]([N:13]2[C@@H:12]([CH:9]([CH3:11])[CH3:10])[CH2:16][O:15][C:14]2=[O:17])[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 1377162,4-DifluoropyrimidineHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one

생성물 1

HCID 86730137HCID 86730137, 화합물수율 33.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 2,4-difluoropyrimidine (3.5 mL, 41 mmol) and (S)-4-isopropyloxazolidin-2-one (5.3 g 41 mmol) in 30 mL DMF was cooled to 0° C. under N2 atmosphere. NaH (2.1 g of 60% suspension, 53 mmol) was slowly added. Bubbling exotherm observed. Internal temp was kept below 5° C. After 5 minutes, cold bath was removed. Reaction mixture (a sandy suspension) was allowed to warm to room temp and stir 18 h. The reaction mixture was diluted with water (100 mL) and extracted with (3×75 mL) EtOAc. Organic layer was washed with 50 mL each water, and brine. Dried over Na2SO4, and concentrated on silica gel in vacuo. Column chromatography (EtOAc/heptane 10 to 100% gradient) gave 3.1 g (S)-3-(2-fluoropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (IV) as a crystalline white solid (33%). 1H NMR (400 MHz, CDCl3) δ 8.50 (dd, J=5.8, 2.2 Hz, 1H), 8.19 (dd, J=5.8, 3.8 Hz, 1H), 4.79 (dt, J=8.1, 3.5 Hz, 1H), 4.48-4.34 (m, 2H), 2.64 (heptd, J=7.0, 3.6 Hz, 1H), 1.01 (d, J=7.0 Hz, 3H), 0.90 (d, J=6.9 Hz, 3H). MS m/z 471.8 and 471.8 (M+H)+.

후처리

  1. customBubbling exotherm
  2. customwas kept below 5° C
  3. customcold bath was removed
  4. customReaction mixture (a sandy suspension)
  5. extractionextracted with (3×75 mL) EtOAc
  6. washOrganic layer was washed with 50 mL each water, and brine
  7. dry with materialDried over Na2SO4
  8. concentrationconcentrated on silica gel in vacuo

출처 및 근거

ORD 기록
ord-695de0d84b834df996520af7df416920
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957068B2

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