Acetonitrile → 7-(5-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydro-N-(3-methoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine

HRID 971262노트

반응식

HRID 971262 반응식
Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27].C(#N)C.I.C(=O)(O)[O-].[Na+]>>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([N:9]2[CH2:10][CH2:11][C:3]3[C:2]([NH:27][C:26]4[CH:28]=[CH:29][CH:30]=[C:24]([O:23][CH3:22])[CH:25]=4)=[N:7][CH:6]=[N:5][C:4]=3[CH2:8]2)=[N:13][CH:14]=1

참가 물질

6

반응물 5

HCID 6342AcetonitrileHCID 108243-MethoxyanilineHCID 24841Hydrogen iodideHCID 516892Sodium BicarbonateHCID 590214804-Chloro-7-(5-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

생성물 1

HCID 120041287-(5-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydro-N-(3-methoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine수율 443.9%

반응 조건

온도
160 °C

실험 절차

A mixture of 4-chloro-7-(5-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (0.035 g, 0.00011 mol), 3-methoxyaniline (0.018 mL, 0.00016 mol) in acetonitrile (0.5 mL, 0.01 mol) and 47% HI (0.05 mL, 0.0007 mol) was heated at 160° C. for 20 minutes in in a sealed tube via microwave. After cooling to r.t., the mixture was poured into saturated aqueous sodium bicarbonate (5 mL) and extracted with ethyl acetate (10 mL). The organic layer was washed with brine and dried over magnesium sulfate. Concentrated to leave a brown solid. Residue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%) to give 0.196 g of a white foam.

후처리

  1. temperatureAfter cooling to r.t.
  2. extractionextracted with ethyl acetate (10 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentrated
  6. customto leave a brown solid
  7. customResidue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%)

출처 및 근거

ORD 기록
ord-5a3523937d8145d8a8faf8dc80f6cd0c
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312330B2

반응 노트

불러오는 중…