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Chloroacetaldehyde → 7-(1-Methyl-1H-pyrazol-4-yl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

HRID 1852959
ノート
印刷プレビュー

反応式

HRID 1852959 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:17]=3)[N:10]=[C:9]([NH2:26])[CH:8]=2)[CH:4]=[N:3]1.[CH3:27][C:28]([O-])=O.[Na+].ClCC=O.C([O-])(O)=O.[Na+]>P([O-])([O-])([O-])=O.CCO.CCOC(C)=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:23])([CH3:25])[CH3:24])[CH:17]=3)[N:10]3[CH:27]=[CH:28][N:26]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 33Chloroacetaldehyde2 回HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 674585736-(1-methyl-1H-pyrazol-4-yl)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrimidin-4-amine

生成物 1

HCID 674576157-(1-Methyl-1H-pyrazol-4-yl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine収率 41.2%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 1061Phosphate溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

6-(1-methyl-1H-pyrazol-4-yl)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrimidin-4-amine (2.0 g, 5.4 mmol) was suspended in a mixture of 40 mL of pH 7 phosphate buffer and 16 mL of EtOH. To the milky white mixture was added NaOAc (0.79 g, 9.7 mmol) followed by 2-chloroacetaldehyde (1.0 mL, 8.1 mmol). The reaction mixture was then heated to 95° C. After 5 hours, the reaction was incomplete and another portion of 2-chloroacetaldehyde (0.10 mL, 0.81 mmol) was added and stirred for another 1 hour. After cooling, the reaction mixture was diluted in EtOAc and saturated NaHCO3. After separation, the organic layer was washed with brine, dried with MgSO4, filtered and concentrated in vacuo. The residue was diluted in diethyl ether, sonicated, and filtered to afford 0.88 g of 7-(1-methyl-1H-pyrazol-4-yl)-5-(1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine as an off-white solid. Additional product was obtained by concentration of the filtrate and purification by silica chromatography using 0-10% MeOH/EtOAc. This afforded another 0.80 g of the intermediate. MS (apci) m/z=396.2 (M+H).

後処理

  1. temperatureAfter cooling
  2. customAfter separation
  3. washthe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted in diethyl ether
  8. customsonicated
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-faad69cbac0d4b9db54e7e03b25d1a94
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962596B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート