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

HRID 1789938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789938
[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

Komponenten

5

Edukt 2

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

Produkt 2

HCID 222AmmoniaHCID 102719362-[[7-Amino-2-[[(2,3-difluorophenyl)methyl]thio]-4-pteridinyl]amino]-1,3-propanediolAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13901-MethylimidazoleLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f99cb156d7224367b03f8c191091bbb7
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071193B2

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