Chloroform → (2-Fluoro-9-isopropyl-9H-purin-6-yl)pyridine-4-ylmethylamine

HRID 2047668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047668
[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:26]([CH3:28])[CH3:27].C(Cl)(Cl)Cl>CN(C=O)C.CO>[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:26]([CH3:28])[CH3:27])=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:3]=1

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178506017HCID 178506017, Verbindung

Produkt 1

HCID 57433119(2-Fluoro-9-isopropyl-9H-purin-6-yl)pyridine-4-ylmethylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of (2-Fluoro-9H-purin-6-yl)-pyridin-4-ylmethyl-amine (0.6 g, 2.46 mmol) in DMF (10 mL) under an argon atmosphere, at RT, was added K2CO3 (powdered, anhydrous, 1.7 g, 5 eq, 12.3 mmol) followed by 2-bromopropane (2.3 ml, 10 eq, 24.6 mmol). The reaction mixture was stirred at RT for 24 h, when TLC (CHCl3:MeOH; 90:10) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between water (200 ml) and EtOAc (50 ml). The aqueous phase was separated and extracted with more EtOAc (2×50 mL). The bulked organic phase was washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo, and the residue was purified by gradient column chromatography on silica gel, eluted with chloroform:methanol (100:0→95:5), to provide the product as a white solid; Yield: 0.40 g (57%). mp 170-173° C. 1H-NMR (d6-DMSO, 250 MHz): δ 1.49 (6 H, d, J 7.5, —CH(CH3)2), 4.63 (3 H, m, —CH(CH3)2+—HNCH2-Pyr), 7.30, 8.47 (4 H, 2×m, Pyr-H), 8.28 (s, 1 H, —N═CH—N—), 8.97 (1 H, s, br, —HNCH2-Pyr). m/z: 287 ([M+H].

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between water (200 ml) and EtOAc (50 ml)
  3. customThe aqueous phase was separated
  4. extractionextracted with more EtOAc (2×50 mL)
  5. washThe bulked organic phase was washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customthe residue was purified by gradient column chromatography on silica gel
  9. washeluted with chloroform:methanol (100:0→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-ed6e66ef5e3649ca9385e9b5a021ae4c
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592581B2

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