2,3-Dichloropyridine → 6-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydro-N-phenylpyrido[4,3-d]pyrimidin-4-amine

HRID 535347노트

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HRID 535347 반응식
[C:1]1([NH:7][C:8]2[C:9]3[CH2:17][NH:16][CH2:15][CH2:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.CN(C)C(=O)C>[Cl:25][C:24]1[C:19]([N:16]2[CH2:15][CH2:14][C:10]3[N:11]=[CH:12][N:13]=[C:8]([NH:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:9]=3[CH2:17]2)=[N:20][CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 593465585,6,7,8-Tetrahydro-N-phenylpyrido[4,3-d]pyrimidin-4-amine

생성물 1

HCID 593464736-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydro-N-phenylpyrido[4,3-d]pyrimidin-4-amine수율 25.6%

시약·촉매·용매 1

HCID 67000103dioxane N,N-dimethylacetamide용매

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온도
150 °C

실험 절차

5,6,7,8-Tetrahydro-N-phenylpyrido[4,3-d]pyrimidin-4-amine (500 mg, 2.2 mmol) was dissolved in a mixture of dioxane/N,N-dimethylacetamide (4:1) (2 mL). To the mixture was added 2,3-dichloropyridine (423 mg, 2.86 mmol) and N,N-diisopropylethylamine (0.38 mL, 2.2 mmol). The mixture was heated at 150° C. in a microwave (Emrys Optimizer model, Personal Chemistry) for 16 h. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a brown residue. The residue was purified using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as an off-white powder (190 mg).

후처리

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a brown residue
  8. customThe residue was purified

출처 및 근거

ORD 기록
ord-bf1dc1d36def49c18e25a7437f0e8edb
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859545B2

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