Potassium Phosphate, Tribasic → (S)-N2-[1-(4-Fluorophenyl)ethyl]-N4-(pyrazin-2-yl)-6-(thiazol-5-yl)pyrimidine-2,4-diamine

HRID 1187702ノート

反応式

HRID 1187702 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[S:12][CH:11]=[N:10][CH:9]=2)[N:5]=[C:4]([NH:13][C@H:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[N:3]=1.[NH2:23][C:24]1[CH:29]=[N:28][CH:27]=[CH:26][N:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C@@H:14]([NH:13][C:4]2[N:3]=[C:2]([NH:23][C:24]3[CH:29]=[N:28][CH:27]=[CH:26][N:25]=3)[CH:7]=[C:6]([C:8]3[S:12][CH:11]=[N:10][CH:9]=3)[N:5]=2)[CH3:15])=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 78747AminopyrazineHCID 86659392(S)-4-chloro-N-[1-(4-fluorophenyl)ethyl]-6-(thiazol-5-yl)pyrimidine-2-amine

生成物 1

HCID 56837787(S)-N2-[1-(4-Fluorophenyl)ethyl]-N4-(pyrazin-2-yl)-6-(thiazol-5-yl)pyrimidine-2,4-diamine収率 57.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To 155 mg of (S)-4-chloro-N-[1-(4-fluorophenyl)ethyl]-6-(thiazol-5-yl)pyrimidine-2-amine, 53 mg of 2-aminopyrazine, 72 mg of 4,5-bis(diphenylphosphino)-9,9′-dimethylxanthene, 196 mg of tripotassium phosphate and 81 mg of tris(dibenzylideneacetone)(chloroform)dipalladium, was added 4 ml of 1,4-dioxane, and the mixture was subjected to degassing, and substituted by argon gas, and then was stirred at 100° C. for 5 hours. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 105 mg of the objective compound as pale yellow powder.

後処理

  1. customto degassing
  2. additionThe reaction solution was diluted with ethyl acetate
  3. washThe solution was washed in turn with water and brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a2a46c609f6144308d5fad6d82acefed
出典データセット
uspto-grants-2014_03
特許番号
US08673891B2

反応ノート

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