Potassium Carbonate → HCID 178437121、化合物

HRID 577184ノート

反応式

HRID 577184 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 595893414-(Bromomethyl)-3-ethylpyridineHCID 178516148HCID 178516148、化合物

生成物 1

HCID 178437121HCID 178437121、化合物収率 14.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e691cc05a1bd4561af436948e9febef3
出典データセット
uspto-grants-2015_05
特許番号
US09040538B2

反応ノート

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