Thiazole → 3-(2-Fluorobenzyl)-7-(2-thiazolyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine

HRID 750511

Reaktionsgleichung

Reaktionsgleichung von HRID 750511
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.Cl[C:12]1[C:13]2[N:21]=[N:20][N:19]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:14]=2[N:15]=[C:16]([NH2:18])[N:17]=1>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][N:19]1[C:14]2[N:15]=[C:16]([NH2:18])[N:17]=[C:12]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)[C:13]=2[N:21]=[N:20]1

Komponenten

7

Edukt 3

HCID 9256ThiazoleHCID 218745675-amino-7-chloro-3-(2-fluorobenzyl)-3H-1,2,3-triazolo[4,5-d]pyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 98585783-(2-Fluorobenzyl)-7-(2-thiazolyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of thiazole (0.10 mL, 1.43 mmol) in dry THF (5 mL) at −78° C., under argon was treated with n-BuLi (0.9 mL, 1.6-M in hexanes, 1.43 mmol), stirred for 30 min, treated with a solution of ZnCl2 (1.8 mL, 1-M in Et20, 1.80 mmol) and allowed to warm gradually to room temperature. The mixture was treated with 7-chloro-3-(2-fluorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (200 mg, 0.714 mmol) and Pd(PPh3)4 (50 mg), refluxed for 2 h and partitioned between saturated NH4Cl (20 mL) and EtOAc (20 mL). The organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; iso-hexane:EtOAc (1:1)] to give the title compound (70 mg, 30%) as a cream solid.

Aufarbeitung

  1. temperaturerefluxed for 2 h
  2. custompartitioned between saturated NH4Cl (20 mL) and EtOAc (20 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; iso-hexane:EtOAc (1:1)]

Quellen und Nachweise

ORD-Eintrag
ord-9eb9a801b5c74c75805255732d5e98cf
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405219B2

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