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Diisopropylethylamine → 5-Chloro-2-(4-((6-methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

HRID 657791
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HRID 657791 반응식
[CH3:1][O:2][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.[Cl:21][C:22]1[CH:23]=[CH:24][C:25](F)=[C:26]([CH:29]=1)[C:27]#[N:28].C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CCOC(C)=O.C(#N)C>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([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]([O:2][CH3:1])=[CH:4][CH:5]=4)[C:12]=3[CH2:20]2)=[C:26]([CH:29]=1)[C:27]#[N:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 936535-Chloro-2-fluorobenzonitrile2회HCID 516892Sodium BicarbonateHCID 59840689N-((6-methoxypyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

생성물 1

HCID 250624095-Chloro-2-(4-((6-methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile수율 44.5%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of N-((6-methoxypyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (440 mg, 1.6 mmol), 5-chloro-2-fluorobenzonitrile (630 mg, 4.0 mmol), N,N-diisopropylethylamine (560 uL, 3.2 mmol), and acetonitrile (4.0 mL) was subjected to microwave irradiation at 180° C. for 4 h. After that an additional 5-chloro-2-fluorobenzonitrile (400 mg) was added and the mixture was subjected to microwave irradiation at 180° C. for another 2 h. After cooling, the mixture was treated with aq. NaHCO3 and EtOAc (100 mL). The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column (EtOAc: 100%) and the obtained solid was washed with ether to yield an off-white solid (290 mg, 44%).

후처리

  1. customirradiation at 180° C. for 4 h
  2. customirradiation at 180° C. for another 2 h
  3. temperatureAfter cooling
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column (EtOAc: 100%)
  9. washthe obtained solid was washed with ether

출처 및 근거

ORD 기록
ord-459226c8ba004785819a30c1b67ae24d
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08076345B2

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