Ammonium Chloride → 10-Hydroxy-10-(3-methoxy-2-methylpropyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indole

HRID 2231821ノート

反応式

HRID 2231821 の反応式
Br[CH2:2][CH:3]([CH3:7])[CH2:4][O:5][CH3:6].[Mg].[N:9]1[CH2:10][CH2:11][CH2:12][N:13]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15](=[O:22])[C:14]=12.[Cl-].[NH4+]>CCOCC.ClCCCl>[OH:22][C:15]1([CH2:2][CH:3]([CH3:7])[CH2:4][O:5][CH3:6])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[N:13]2[CH2:12][CH2:11][CH2:10][N:9]=[C:14]12

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 141813833,4-Dihydropyrimido(1,2-a)indol-10(2h)-oneHCID 212848141-Bromo-3-methoxy-2-methylpropane

生成物 1

HCID 1418140110-Hydroxy-10-(3-methoxy-2-methylpropyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indole

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

1-Bromo-3-methoxy-2-methylpropane (10.02 g) in ether (50 ml) was added dropwise over 20 minutes to magnesium turnings (1.46 g) in ether (10 ml). The mixture was stirred under argon at room temperature for 30 minutes, cooled to 0° and 3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (3.72 g) in dry 1,2-dichloroethane (20 ml) added dropwise over 20 minutes. The solution was stirred under argon at 0° for 1 hour, poured onto a swirling mixture of ice (100 ml) and saturated aqueous ammonium chloride (60 ml). The mixture was stirred for 20 minutes and concentrated in vacuo. The aqueous residue was extracted with chloroform (3×100 ml). The extracts were dried (Na2SO4) and concentrated in vacuo. Ether (20 ml) was added and the product was filtered and recrystallised from ethyl acetate to give the title compound as the free base (2.85 g), m.p. 162°-167° C. The free base was acidified with ethereal HCl to give the title compound as the hydrochloride, m.p. 244° (dec.).

後処理

  1. temperaturecooled to 0°
  2. stirringThe solution was stirred under argon at 0° for 1 hour
  3. stirringThe mixture was stirred for 20 minutes
  4. concentrationconcentrated in vacuo
  5. extractionThe aqueous residue was extracted with chloroform (3×100 ml)
  6. dry with materialThe extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. additionEther (20 ml) was added
  9. filtrationthe product was filtered
  10. customrecrystallised from ethyl acetate

出典と根拠

ORDレコード
ord-b7217d2fe0cb451b86ef71bc27825076
出典データセット
uspto-grants-1988_11
特許番号
US04784996

反応ノート

読み込み中…