Triethylamine → 4-chloro-8-(2,4-difluorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1454443노트

반응식

HRID 1454443 반응식
Cl[C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.CCN(CC)CC.[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=1[NH2:23].C[O:30][C:31]([CH2:33]P(=O)(OCC(F)(F)F)OCC(F)(F)F)=O>C1COCC1.ClCCl>[Cl:10][C:6]1[C:7]2[CH:8]=[CH:33][C:31](=[O:30])[N:23]([C:22]3[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:21]=3[F:20])[C:2]=2[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 184894Nsc 634137HCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

생성물 1

HCID 119513484-chloro-8-(2,4-difluorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one수율 52%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (1.0 g, 4.5 mmol) and Et3N (1.26 mL, 9.0 mmol) in THF (25 mL) was mixed with 2,4-difluoroaniline (0.50 mL, 4.9 mmol). The resultant mixture was stirred at room temperature for 2 hours before bis(2,2,2-trifluoroethyl) (methoxycarbonyl-methyl)phosphonate (0.95 mL, 4.5 mmol) was added. After stirring at room temperature for additional 48 hours, the mixture was diluted with dichloromethane (50 mL) and then washed with H2O (2×25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. This crude product was applied to flash chromatography (EtOAc/Hexane, 1:5) to provide the title compound (0.79 g, 52%): MS (ES) m/z 340 (M+H)+; 1H-NMR(CDCl3) δ 2.24 (s, 3H), 6.79 (d, J=9.8 Hz, 1H), 7.06 (m, 2H), 7.29 (m, 1H), 8.03 (d, J=9.8 Hz, 1H).

후처리

  1. additionwas added
  2. washwashed with H2O (2×25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-017781cae1574539a9d09a57efff2a42
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07479558B2

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