Potassium Carbonate → 2,5-dichloro-N-[(1S)-1-(3-methoxyphenyl)ethyl]pyrimidin-4-amine

HRID 1614956ノート

反応式

HRID 1614956 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:9]([NH2:11])[CH3:10])[CH:6]=[CH:7][CH:8]=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>[Cl:12][C:13]1[N:18]=[C:17]([NH:11][C@H:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:10])[C:16]([Cl:20])=[CH:15][N:14]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 7020761(S)-1-(3-methoxyphenyl)ethylamine

生成物 1

HCID 584678612,5-dichloro-N-[(1S)-1-(3-methoxyphenyl)ethyl]pyrimidin-4-amine収率 96%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (1S)-1-(3-methoxyphenyl)ethanamine (1.50 g, 9.92 mol) (S-isomer, >99% ee purity) and 2,4,5-trichloropyrimidine (1.19 mL, 10.4 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.1 g, 30 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. Then 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 then dried (Na2SO4), filtered, and concentrated to give the desired product as a light yellow thick oil (2.84 g, 96%). LCMS for C13H14Cl2N3O (M+H)+: m/z=298.0, 300.0, 302.0 (9:6:1).

後処理

  1. customThe reaction was quenched with water
  2. additionThen EtOAc 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
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-1157df33814b43f0b5c42d0713daec4b
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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