Potassium Carbonate → HCID 178437620, 화합물

HRID 630196노트

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HRID 630196 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[C:22]([CH2:28][CH3:29])=[N:23][CH:24]=[CH:25][C:26]=1[Cl:27]>CN(C=O)C>[Cl:27][C:26]1[CH:25]=[CH:24][N:23]=[C:22]([CH2:28][CH3:29])[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 595895013-(Bromomethyl)-4-chloro-2-ethylpyridineHCID 178516148HCID 178516148, 화합물

생성물 1

HCID 178437620HCID 178437620, 화합물수율 25%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (884 mg, 4.5 mmol) was dissolved in anhydrous DMF (30 mL), and then potassium carbonate (1.87 g, 13.5 mmol) and 3-(bromomethyl)-4-chloro-2-ethylpyridine (5.4 mmol) in DMF (10 mL) were added. The 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 3-10% DCM/MeOH to afford 2-{[(4-chloro-2-ethylpyridin-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (391 mg, 25% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 1.19 (t, J=7.4 Hz, 3H), 2.93 (q, J=7.4 Hz, 2H), 4.66 (s, 2H), 6.69 (s, 1H), 7.43 (d, J=5.3 Hz, 1H), 8.40 (d, J=5.3 Hz, 1H).

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 3-10% DCM/MeOH

출처 및 근거

ORD 기록
ord-465c7a77f38249c9b188d2bec83c3d1e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315521B2

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