Serinol → 2-[[7-Amino-2-[[(2,3-difluorophenyl)methyl]thio]-4-pteridinyl]amino]-1,3-propanediol

HRID 1789938ノート

反応式

HRID 1789938 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:20]=[C:19](SCC2C=CC=C(F)C=2F)[C:18]2[C:13](=[N:14][C:15]([NH2:31])=[CH:16][N:17]=2)[N:12]=1.[NH2:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35]>CN1C=CN=C1>[NH3:12].[NH2:31][C:15]1[N:14]=[C:13]2[C:18]([C:19]([NH:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35])=[N:20][C:11]([S:10][CH2:9][C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])=[N:12]2)=[N:17][CH:16]=1

参加物

5

反応物 2

HCID 68294SerinolHCID 220370392,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7-pteridinamine

生成物 2

HCID 222AmmoniaHCID 102719362-[[7-Amino-2-[[(2,3-difluorophenyl)methyl]thio]-4-pteridinyl]amino]-1,3-propanediol収率 39.2%

試薬・触媒・溶媒 1

HCID 13901-Methylimidazole溶媒

実験手順

A solution of the product from example 1, step (c) (0.12 g) and serinol (330 mg) in 1-methylimidazole (1 ml) was heated at 130° C. for 90 minutes. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic phase was dried over magnesium sulphate, filtered and evaporated to give a brown solid which was purified by silica gel flash column chromatography, eluting with 200:20:1 dichloromethane:methanol:880 ammonia solution, to give the title compound as a pale brown solid (0.02 g).

後処理

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown solid which
  7. customwas purified by silica gel flash column chromatography
  8. washeluting with 200:20:1 dichloromethane

出典と根拠

ORDレコード
ord-f99cb156d7224367b03f8c191091bbb7
出典データセット
uspto-grants-2006_07
特許番号
US07071193B2

反応ノート

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