2,6-Dimethylbenzoyl chloride → N'-[1-(2,6-dimethylbenzoyl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethylformamidine

HRID 1260412노트

반응식

HRID 1260412 반응식
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:16]=1[C:17](Cl)=[O:18]>N1C=CC=CC=1>[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:16]=1[C:17]([N:6]1[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]1=[O:8])=[O:18]

참가 물질

4

반응물 2

HCID 890962,6-Dimethylbenzoyl chlorideHCID 178484257HCID 178484257, 화합물

생성물 1

HCID 66954641N'-[1-(2,6-dimethylbenzoyl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethylformamidine수율 37%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
40 °C

실험 절차

To an 8 mL screw-cap vial were added pyridine (2 mL), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), and 2,6-dimethylbenzoyl chloride (102 mg, 0.60 mmol). The mixture was heated to 40° C. for 2 h, evaporated to dryness, and partitioned between ethyl acetate (EtOAc) and water (H2O). The organic phase was dried over magnesium sulfate (MgSO4), filtered, evaporated, and the residue was purified by reverse phase chromatography to yield the title compound as a white solid (63 mg, 37%): mp 120-150° C.; 1H NMR (300 MHz, CDCl3) δ 8.81 (s, 1H), 8.22 (d, J=6.04 Hz, 1H), 7.23-7.17 (m, 1H), 7.07-7.01 (m, 2H), 3.27 (s, 3H), 3.24 (s, 3H), 2.24 (s, 6H); ESIMS m/z 317 ([M+H]+).

후처리

  1. customTo an 8 mL screw-cap vial
  2. customevaporated to dryness
  3. custompartitioned between ethyl acetate (EtOAc) and water (H2O)
  4. dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by reverse phase chromatography

출처 및 근거

ORD 기록
ord-8925733bb8854706b102058df8f5f1e6
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470839B2

반응 노트

불러오는 중…