Cesium carbonate → {[3-(3,4-dimethoxybenzyl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl]oxy}acetonitrile

HRID 1022514노트

반응식

HRID 1022514 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[N:9]([CH:19]2[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]2)[C:8]1=[O:27].Br[CH2:34][C:35]#[N:36].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:34][C:35]#[N:36])[CH:14]=2)[N:9]([CH:19]2[CH2:20][CH2:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24]2)[C:8]1=[O:27]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 667326983-(3,4-dimethoxybenzyl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-6-hydroxyquinazoline-2,4(1H,3H)-dione

생성물 1

HCID 49764282{[3-(3,4-dimethoxybenzyl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl]oxy}acetonitrile수율 72.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 0.055 g of the compound obtained in Step 18.2, 0.017 g of bromoacetonitrile and 0.078 g of Cs2CO3 in 2 ml of DMF is irradiated in a microwave field for 15 minutes at 100° C. The reaction mixture is evaporated under reduced pressure. The residue is taken up in DCM, washed with water, dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with an MeOH/DCM mixture from (0.5/99.5, v/v) to (5/95, v/v), to give 0.043 g of the expected product.

후처리

  1. customis irradiated in a microwave field for 15 minutes at 100° C
  2. customThe reaction mixture is evaporated under reduced pressure
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel
  8. washeluting with an MeOH/DCM mixture from (0.5/99.5

출처 및 근거

ORD 기록
ord-3d0d3137c00342a9bdab733d57de377f
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722659B2

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