Potassium Carbonate → N-(3-Bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amine

HRID 1614974ノート

反応式

HRID 1614974 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][NH2:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([Cl:20])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1)[CH2:10][NH:11][C:15]1[C:16]([Cl:20])=[CH:17][N:18]=[C:13]([Cl:12])[N:14]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 534144413-Bromo-5-methoxybenzenemethanamine

生成物 1

HCID 58467901N-(3-Bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amine収率 87%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(3-bromo-5-methoxyphenyl)methanamine (2.57 g, 11.9 mmol) and 2,4,5-trichloropyrimidine (2.4 g, 13 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (3.3 g, 24 mmol). The resultant mixture was stirred overnight at room temperature. The reaction mixture was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography to give the desired product (3.7 g, 87%). LCMS for C12H10BrCl2N3O (M+H)+: m/z=361.9, 363.9.

後処理

  1. customThe reaction mixture was quenched with water
  2. additionEtOAc was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washThe combined organic layers were washed with water and brine successively
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-7aa0bc8e71ef4a94ba0020ac5fcddb3f
出典データセット
uspto-grants-2014_07
特許番号
US08765727B2

反応ノート

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