Thiazole → 2-Chloro-4-(2-thiazolyl)thieno[3,2-d]pyrimidine

HRID 131193

Reaktionsgleichung

Reaktionsgleichung von HRID 131193
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[Cl:11][C:12]1[N:13]=[C:14](Cl)[C:15]2[S:20][CH:19]=[CH:18][C:16]=2[N:17]=1>C1COCC1.[NH4+].[Cl-].[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>[Cl:11][C:12]1[N:13]=[C:14]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[C:15]2[S:20][CH:19]=[CH:18][C:16]=2[N:17]=1

Komponenten

8

Edukt 3

HCID 9256ThiazoleHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 444495652-Chloro-4-(2-thiazolyl)thieno[3,2-d]pyrimidineAusbeute 29,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3007855ZincchlorideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A stirred solution of thiazole (0.14 mL, 2 mmol) in dry THF (10 mL) at −78° C., under argon was treated with n-BuLi (1.6-M in hexanes, 1.3 mL, 2 mmol), stirred for 30 min, treated with a solution of ZnCl2 (1.0-M in Et2O, 2.0 mL, 2 mmol) and allowed to warm gradually to room temperature. The mixture was treated with a solution of 2,4-dichlorothieno[3,2-d]pyrimidine (205 mg, 1 mmol) in THF (5 mL) then Pd(PPh3)4 (100 mg, 10 mol %) refluxed for 17 h, cooled, diluted with saturated NH4Cl solution and extracted with EtOAc. The organic extracts were dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; isohexane:CH2Cl2 (2:1)] to give the title compound (75 mg, 26%) as a white solid.

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; isohexane:CH2Cl2 (2:1)]

Quellen und Nachweise

ORD-Eintrag
ord-96f2a38021b84d41893b9f04c1daf11c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384949B2

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