Ammonium Chloride → Bromo-9-(2-hydroxy-4-phenyl-butyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

HRID 33980

反応式

HRID 33980 の反応式
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH2:11][NH:12][C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[CH2:19]([CH:27]1[CH2:29][O:28]1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:29][CH:27]([OH:28])[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:5]2=[N:4][C:3]=1[C:13]1[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 1359552-(2-Phenylethyl)oxiraneHCID 2733832Lithium HexamethyldisilazideHCID 1360923803-Bromo-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

生成物 1

HCID 59796509Bromo-9-(2-hydroxy-4-phenyl-butyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-Bromo-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (0.45 g, 1.46 mmol) and 2-Phenethyl-oxirane (0.65 g, 4.4 mmol) in DMF (20 mL) was treated LiHMDS (5 mL, 5 mml). The mixture was heated at 90 C for 1 h and was cooled to room temperature. Saturated NH4Cl (50 mL) was added and the mixture was extracted with CH2Cl2 (3×20 mL). The organic phase was washed with H2O (3×), dried (Na2SO4), and concentrated. The resulting brown oil was chromatographed on silica with 1-5% (2N NH3-MeOH)/CH2Cl2 to afford the product as a white solid. M+1 457.

後処理

  1. temperatureThe mixture was heated at 90 C for 1 h
  2. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
  3. washThe organic phase was washed with H2O (3×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting brown oil was chromatographed on silica with 1-5% (2N NH3-MeOH)/CH2Cl2

出典と根拠

ORDレコード
ord-bbb7399147164b5c850f0512570b1803
出典データセット
uspto-grants-2008_09
特許番号
US07429594B2

関連ノート

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