Potassium Carbonate → tert-Butyl [5-(2-{3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate

HRID 541871ノート

反応式

HRID 541871 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[N:30]=[C:29](Cl)[C:28]([F:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:25]1[N:30]=[C:29]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]3[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:13]=[N:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=2)[C:28]([F:32])=[CH:27][N:26]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 57961822tert-Butyl {5-[2-(3-aminophenyl)ethyl]pyridin-3-yl}carbamate

生成物 1

HCID 57962649tert-Butyl [5-(2-{3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate収率 21.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of tert-butyl {5-[2-(3-aminophenyl)ethyl]pyridin-3-yl}carbamate (0.20 g, 0.64 mmol) (prepared in Example C19, step B) and 2,4-dichloro-5-fluoropyrimidine (200 mg, 1.2 mmol) in N,N-dimethylformamide (4 mL) was added potassium carbonate (0.430 g, 3.1 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc once. The combined organic layers were washed with water and brine, and then dried (Na2SO4), filtered, and concentrated. The crude was purified by silica gel column chromatography to give the desired product as a light yellow oil (60 mg, 20%). LCMS for C22H24ClFN5O2 (M+H)+: m/z=444.0.

後処理

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

出典と根拠

ORDレコード
ord-d6b42f62d334472292429e391aee633a
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

反応ノート

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