Sodium hydride → HCID 20451291, Verbindung

HRID 1463063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463063
[F:1][C:2]([F:18])([F:17])[CH2:3][N:4]=[C:5]([NH2:16])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1.[OH:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]([F:18])([F:17])[CH2:3][N:4]=[C:5]([NH2:16])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[N:8]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 72922PyripropanolHCID 212797752-Methylsulphinyl-4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimidine

Produkt 1

HCID 20451291HCID 20451291, VerbindungAusbeute 23,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-methylsulphinylpyrimidine (150 mg.) was added to a stirred mixture of 2-(3-hydroxypropyl)pyridine (82 mg.), a 50% w/w dispersion of sodium hydride in oil (30 mg.) and DMF (2 ml.) and the mixture heated at 90° for 1 hour. The mixture was evaporated to dryness and the residue partitioned between water and EtOAc. The EtOAc phase was dried and evaporated to dryness. The residue was subjected to preparative thin layer chromatography using EtOAc/MeOH/aqueous ammonia (s.g. 0.88) 6:1:0.5 v/v/v as developing solvent. The band having Rf 0.6 was eluted with MeOH and the MeOH evaporated to dryness to give 2-[3-(4-[2-(2,2,2-trifluoroethyl)guanidino]-pyrimid-2-yloxy)propyl]pyridine (45 mg.), which was characterised as the bis hydrogen maleate salt, m.p. 118°-120° (after crystallisation from acetone/ether).

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. customthe residue partitioned between water and EtOAc
  3. dry with materialThe EtOAc phase was dried
  4. customevaporated to dryness
  5. washwas eluted with MeOH
  6. customthe MeOH evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bdd407ac1a494f84883d101c61c72a88
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04463005

Notizen zur Reaktion

Wird geladen…