Potassium Carbonate → HCID 178437121, 화합물

HRID 630226노트

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HRID 630226 반응식
[SH:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[CH2:27][CH3:28]>CN(C=O)C>[CH2:27]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:21]=1[CH2:20][S:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([F:12])([F:10])[F:11])[N:3]=1)[CH3:28]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 595893414-(Bromomethyl)-3-ethylpyridineHCID 178516148HCID 178516148, 화합물

생성물 1

HCID 178437121HCID 178437121, 화합물수율 14.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (1.56 g, 8.0 mmol) was dissolved in anhydrous DMF (50 mL), and then potassium carbonate (3.3 g, 23.9 mmol) and 4-(bromomethyl)-3-ethylpyridine (10.3 mmol) in DMF (10 mL) were added. The reaction mixture was stirred overnight at room temperature. The solid was removed by filtration and washed with methanol, and the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 3-12% DCM/MeOH to afford 2-{[(3-ethylpyridin-4-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (357 mg, 14% yield for 3 steps); 1H NMR (500 MHz, DMSO-d6): δ 1.21 (t, J=7.5 Hz, 3H), 2.75 (q, J=7.5 Hz, 2H), 4.46 (s, 2H), 6.65 (s, 1H), 7.41 (d, J=5.1 Hz, 1H), 8.34 (d, J=5.0 Hz, 1H), 8.42 (s, 1H); LRMS (ES+) m/z 316 (100%, M+1).

후처리

  1. customThe solid was removed by filtration
  2. washwashed with methanol
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 3-12% DCM/MeOH

출처 및 근거

ORD 기록
ord-f12058c9b7e647f9a78fd8258777503c
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315521B2

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