Ethyl Acetate → US9296747, Example 4

HRID 930501노트

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HRID 930501 반응식
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1.CO[C:22]1[CH:23]=[C:24]([CH:26]=[C:27](OC)[C:28]=1OC)[NH2:25].CCOC(C)=O>C(O)(C)C>[C:24]1([NH:25][C:2]2[N:3]=[CH:4][C:5]3[CH2:11][N:10]([C:12]([C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)=[O:13])[CH2:9][CH2:8][C:6]=3[N:7]=2)[CH:26]=[CH:27][CH:28]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 322853,4,5-TrimethoxyanilineHCID 118970896(2-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)(pyridin-3-yl)methanone

생성물 1

HCID 118970902US9296747, Example 4수율 54.8%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
60 °C

실험 절차

A solution of (2-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)(pyridin-3-yl)methanone, Intermediate 5 (0.025 g, 0.091 mmol) in isopropanol (0.1 mL) was treated with 3,4,5-trimethoxyaniline (0.021 g, 0.0498 mmol). The resulting mixture was heated to 60° C. and allowed to stir overnight. After being allowed to cool to room temperature EtOAc (10 mL) was added to the reaction mixture, and the resulting solution was then washed twice with brine (10 mL). The combined aqueous layers were washed once with EtOAc (10 mL). The organic layers were combined, then dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The resulting crude residue was then purified over silica using a MeOH/CHCl3 gradient. The desired product was obtained in 54.8% yield (0.021 g, 0.049 mmol).

후처리

  1. additionwas added to the reaction mixture
  2. washthe resulting solution was then washed twice with brine (10 mL)
  3. washThe combined aqueous layers were washed once with EtOAc (10 mL)
  4. dry with materialdried over anhydrous Na2SO4(s)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude residue was then purified over silica using a MeOH/CHCl3 gradient

출처 및 근거

ORD 기록
ord-8b514acc7d8346dfae73bed418993dbe
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296747B1

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