Dimethylformamide → 5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

HRID 1365806

Reaktionsgleichung

Reaktionsgleichung von HRID 1365806
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.C([N-]C(C)C)(C)C.[Li+].CN(C)[CH:27]=[O:28].C(Cl)Cl>O1CCCC1.CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:5]2[N:10]=[C:9]([CH:27]=[O:28])[S:8][C:6]=2[N:7]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 2724682Lithium diisopropylamideHCID 576853854-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine

Produkt 1

HCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 22742125Tetrahydrofuran heptane ethylbenzolLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine was slurried in tetrahydrofuran and cooled to −78° C. under nitrogen. Two equivalents of 2M lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene was added slowly and the solution was stirred for 30 minutes. dimethylformamide (6 eq) was added and the solution was stirred at −78° C. for an additional one hour. The solution was warmed to 0° C. and ice cold 0.1N hydrochloric acid was added and the solution was warmed to room temperature before extraction with methylene chloride. The organic layer was dried with sodium sulfate and concentrated to give 5-chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde.

Aufarbeitung

  1. stirringthe solution was stirred at −78° C. for an additional one hour
  2. temperatureThe solution was warmed to 0° C.
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ada90689861e4a13a80e6bb74acd5f57
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893059B2

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