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Hydrochloric Acid → Methyl Hydroxyethyl Piperazinyl Methyl Pyrimidinylamino Thiazolecarboxylate

HRID 515246
ノート
印刷プレビュー

反応式

HRID 515246 の反応式
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]2)[CH:3]=1.[NH2:18][C:19]1[S:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[OH:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][N:9]([C:4]2[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:18][C:19]3[S:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:23]=3)[CH:3]=2)[CH2:10][CH2:11]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 238005Methyl 2-aminothiazole-5-carboxylate2 回HCID 634876Binap, (A+-)-HCID 144795582-(4-(6-Chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol2 回

生成物 1

HCID 49821888
Methyl Hydroxyethyl Piperazinyl Methyl Pyrimidinylamino Thiazolecarboxylate
収率 75.3%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol (Compound 4) (25.7 g, 0.1 mol), methyl 2-aminothiazole-5-formate (Compound 5) (18.9 g, 0.12 mol), cesium carbonate (45.6 g, 0.14 mol), palladium acetate (2.2 g, 0.01 mol) and BINAP (6.2 g, 0.01 mol) were mixed with toluene (1100 mL) in reaction flask, and heated by stirring to reflux for 16 h. The reactant was cooled and 2 mol/L hydrochloric acid was added and stirred for 10 mins. After vacuum filtration the filtrate was phase-separated and the aqueous phase was extracted by toluene (500 mL). The separated aqueous phase was neutralized by NaOH solution (6 mol/L) at 10-15° C., and then grew the grains for 1 h. After vacuum filtration the cake was rinsed by water to give yellow solid target Compound 6 (28.5 g, yield: 75.2%).

後処理

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. temperatureThe reactant was cooled
  4. stirringstirred for 10 mins
  5. filtrationAfter vacuum filtration the filtrate
  6. customwas phase-separated
  7. extractionthe aqueous phase was extracted by toluene (500 mL)
  8. customwas neutralized by NaOH solution (6 mol/L) at 10-15° C.
  9. customfor 1 h
  10. filtrationAfter vacuum filtration the cake
  11. washwas rinsed by water

出典と根拠

ORDレコード
ord-4c7f379581124faea8f9d7096b64a957
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108954B2

反応ノート

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