Potassium Carbonate → HCID 178437121, 화합물

HRID 577184노트

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HRID 577184 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-e691cc05a1bd4561af436948e9febef3
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040538B2

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