Acetonitrile → 5-bromo-2-(4-((6-(trifluoromethyl)pyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

HRID 657774노트

반응식

HRID 657774 반응식
[F:1][C:2]([F:22])([F:21])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:12]3[CH2:20][NH:19][CH2:18][CH2:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][CH:4]=1.[Br:23][C:24]1[CH:25]=[CH:26][C:27](F)=[C:28]([CH:31]=1)[C:29]#[N:30].C(N(CC)C(C)C)(C)C.C(#N)C>CCOC(C)=O>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([N:19]2[CH2:18][CH2:17][C:13]3[N:14]=[CH:15][N:16]=[C:11]([NH:10][CH2:9][C:6]4[CH:7]=[N:8][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:4][CH:5]=4)[C:12]=3[CH2:20]2)=[C:28]([CH:31]=1)[C:29]#[N:30]

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 27249005-Bromo-2-fluorobenzonitrile3회HCID 59840682N-((6-(trifluoromethyl)pyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

생성물 1

HCID 250618715-bromo-2-(4-((6-(trifluoromethyl)pyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile수율 57.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of N-((6-(trifluoromethyl)pyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (1.0 g, 3.2 mmol), 5-bromo-2-fluorobenzonitrile (0.97 g, 4.8 mmol), N,N-diisopropylethylamine (1.7 mL, 9.7 mmol), and acetonitrile (10 mL) was subjected to microwave irradiation at 180° C. for 2 h. More 5-bromo-2-fluorobenzonitrile (1.0 g) was added and the mixture was subjected to microwave irradiation at 180° C. for another 2 h. Then additional 5-bromo-2-fluorobenzonitrile (1.0 g) was added and the reaction mixture was subjected to microwave irradiation at 180° C. for an additional 2 h. After cooling, the mixture was diluted with EtOAc (100 mL) and washed with aq. Na2CO3 solution and brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel column (100% EtOAc) to yield a light yellow solid (0.90 g, 57%).

후처리

  1. customirradiation at 180° C. for 2 h
  2. customirradiation at 180° C. for another 2 h
  3. customirradiation at 180° C. for an additional 2 h
  4. temperatureAfter cooling
  5. washwashed with aq. Na2CO3 solution and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (100% EtOAc)

출처 및 근거

ORD 기록
ord-f00fdbe4c14c4cec8edc5b231ec9c077
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076345B2

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