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

HRID 19657

반응식

HRID 19657 반응식
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]3[CH2:19][NH:18][CH2:17][CH2:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.Cl[C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.CN(C)C(=O)C>[Cl:29][C:28]1[C:23]([N:18]2[CH2:17][CH2:16][C:12]3[N:13]=[CH:14][N:15]=[C:10]([NH:9][C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:20])[F:21])=[CH:4][CH:5]=4)[C:11]=3[CH2:19]2)=[N:24][CH:25]=[CH:26][CH:27]=1

참가 물질

5

반응물 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 59346476(5,6,7,8-Tetrahydro-pyrido[4,3-d]pyrimidin-4-yl)-(4-trifluoromethylphenyl)amine

생성물 1

HCID 593464886-(3-Chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine수율 26%

시약·촉매·용매 1

HCID 67000103dioxane N,N-dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (700 mg, 3.4 mmol) was dissolved in a mixture of dioxane/N,N-dimethylacetamide (4:1) (2 mL). To the mixture was added 2,3-dichloropyridine (1.5 g, 10.2 mmol) and N,N-diisopropylethylamine (0.87 mL, 5.1 mmol). The mixture was heated in a sealed tube 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 (340 mg, 26%).

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-691de1b9b09b454b9794bf513bd3c423
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745451B2

연결된 노트

불러오는 중…