Potassium Carbonate → 4-Chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine

HRID 965686ノート

反応式

HRID 965686 の反応式
[CH2:1]([C:4]1[C:5]([Cl:12])=[N:6][CH:7]=[N:8][C:9]=1[CH2:10]Br)[CH2:2][CH3:3].[F:13][C:14]1[C:15]([C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)=[N:16][CH:17]=[CH:18][CH:19]=1.[C:25]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:5]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:9]([CH2:10][N:24]2[CH:23]=[CH:22][N:21]=[C:20]2[C:15]2[C:14]([F:13])=[CH:19][CH:18]=[CH:17][N:16]=2)[N:8]=[C:7]([CH3:25])[N:6]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 223131604-Bromomethyl-5-propyl-6-chloro-pyrimidineHCID 223131643-Fluoro-2-(1H-imidazol-2-yl)pyridine

生成物 1

HCID 99977004-Chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-propyl-6-bromomethyl-4-chloro-pyrimidine (1 mmol), 3-fluoro-2-(1H-imidazol-2-yl)-pyridine (163 mg, 1 mmol), and K2CO3 (552 mg, 4 mmol) in DMF (6 mL) is stirred at room temperature overnight. The solvent is removed in vacuo and EtOAc (10 mL) and water (10 mL) are added to the residue. The layers are separated and the aqueous layer is extracted with EtOAc (10 mL). The combined extracts are washed with brine (10 mL), dried (Na2SO4), and evaporated. Preparative TLC separation of the residue with 5% MeOH in CH2Cl2 provides the title compound as a white solid. 1H-NMR (CDCl3) δ: 8.65 (S, 1H), 8.24 (d, 1H), 7.53 (t, 1H), 7.32 (s, 1H), 7.27-7.22 (m, 1H), 7.12 (s, 1H), 5.87 (s, 2H), 2.76 (t, 2H), 1.68-1.54 (m, 2H), 1.01 (t, 3H).

後処理

  1. customThe solvent is removed in vacuo and EtOAc (10 mL) and water (10 mL)
  2. additionare added to the residue
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 mL)
  5. washThe combined extracts are washed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPreparative TLC separation of the residue with 5% MeOH in CH2Cl2

出典と根拠

ORDレコード
ord-5a42393d343846b98da02358bcffce09
出典データセット
uspto-grants-2005_10
特許番号
US06951864B2

反応ノート

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