1-Chloro-2-iodoethane → 5-(2-Ethylbenzoimidazol-1-yl)-2-iodo-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

HRID 1922765

Reaktionsgleichung

Reaktionsgleichung von HRID 1922765
[CH2:1]([C:3]1[N:7]([C:8]2[N:9]=[C:10]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:11]3[N:16]=[CH:15][S:14][C:12]=3[N:13]=2)[C:6]2[CH:23]=[CH:24][CH:25]=[CH:26][C:5]=2[N:4]=1)[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.ClCC[I:40]>C1COCC1>[CH2:1]([C:3]1[N:7]([C:8]2[N:9]=[C:10]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[C:11]3[N:16]=[C:15]([I:40])[S:14][C:12]=3[N:13]=2)[C:6]2[CH:23]=[CH:24][CH:25]=[CH:26][C:5]=2[N:4]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 1364381-Chloro-2-iodoethaneHCID 2733832Lithium HexamethyldisilazideHCID 596056325-(2-Ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

Produkt 1

HCID 596061865-(2-Ethylbenzoimidazol-1-yl)-2-iodo-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

A solution of 5 -(2-ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine (1.92 g, 5.23 mmol) in THF (60 mL) was cooled to −40° C. before the drop wise addition of LiHMDS (6.3 mL, 6.28 mmol, 1 M solution in THF). The resulting mixture was warmed to −5° C. over 30 min then mixture was cooled back to −30° C. before the addition of a solution of 1-chloro-2-iodoethane (2.0 g, 10.47 mmol) in THF (6 mL) The resulting mixture was allowed to warm to 0° C. then quenched with NH4Cl and extracted with EtOAc. The combined organics were washed with brine then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 50-80%) followed by recrystallisation from iPrOAc affording the title compound as a yellow solid (1.58 g, 62%)._LCMS (method A): RT 3.50 min [M+H]+ 493.0

Aufarbeitung

  1. temperatureto warm to 0° C.
  2. customthen quenched with NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialthen dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 50-80%)
  8. customfollowed by recrystallisation from iPrOAc affording the title compound as a yellow solid (1.58 g, 62%)
  9. customRT 3.50 min [M+H]+ 493.0

Quellen und Nachweise

ORD-Eintrag
ord-2995dab65c564bfe9440a6e3e763c92e
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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