Bromoacetone → 6-(Tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyrazine

HRID 216662

反応式

HRID 216662 の反応式
Br[CH2:2][C:3](=O)[CH3:4].[C:6]([SiH2:10][O:11][C:12]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:13]1[N:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1)([CH3:9])([CH3:8])[CH3:7].C([O-])(O)=O.[Na+]>COCCOC.S1(CCCC1)(=O)=O>[C:6]([SiH2:10][O:11][C:12]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:13]1[N:14]=[CH:15][C:16]2[N:17]([CH:2]=[C:3]([CH3:4])[N:19]=2)[CH:18]=1)([CH3:9])([CH3:7])[CH3:8]

参加物

6

反応物 3

HCID 11715BromoacetoneHCID 516892Sodium BicarbonateHCID 178455413HCID 178455413、化合物

生成物 1

HCID 1317297536-(Tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyrazine収率 40%

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 31347Sulfolane溶媒

反応条件

温度
50 °C

実験手順

Bromoacetone (4.3 g, 31.4 mmol, 2.9 equiv) is added to a solution of 5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrazin-2-ylamine (4.0 g, 10.7 mmol) in 1,2-dimethoxyethane (20 ml) and sulfolane (20 ml). The reaction mixture is stirred overnight at 50° C. Then a 10% aqueous solution of NaHCO3 (30 ml) is added, and the mixture is heated to reflux for 1 hour. After cooling, the mixture is extracted three times with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (hexane/EtOAc 3:1) affords the title compound (1.7 g, 40%). 1H NMR (400 MHz, d6-DMSO): δ=8.78 (d, J=0.9 Hz, 1H), 8.43 (d, J=1.4 Hz, 1H), 7.92 (s, 1H), 7.63-7.61 (m, 4H); 7.41-7.35 (m, 6H), 4.72 (s, 2H), 2.34 (s, 3H), 1.00 (s, 9H). MS (ES+): 402 (M+H)+.

後処理

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted three times with EtOAc
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (hexane/EtOAc 3:1)

出典と根拠

ORDレコード
ord-00dcd9c4425745448596a956681b4ee5
出典データセット
uspto-grants-2012_06
特許番号
US08193236B2

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