Triethylamine → HCID 178473466, Verbindung

HRID 471499

Reaktionsgleichung

Reaktionsgleichung von HRID 471499
[NH2:1][C:2]1[C:3]2[C:11]([CH3:12])=[C:10]([CH3:13])[S:9][C:4]=2[NH:5][C:6](=[S:8])[N:7]=1.CCN(CC)CC.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C.CCOC(C)=O>[CH3:12][C:11]1[C:3]2[C:2]([NH:1][C:22](=[O:23])[O:24][CH2:25][CH3:26])=[N:7][C:6](=[S:8])[NH:5][C:4]=2[S:9][C:10]=1[CH3:13]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178435041HCID 178435041, Verbindung

Produkt 1

HCID 178473466HCID 178473466, VerbindungAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 4-amino-5,6-dimethylthieno[2,3-d]pyrimidine-2(1H)-thione (211 mg, 1 mmol) in DMF (5 mL) was added Et3N (0.21 mL, 1.5 mmol) and ethyl chloroformate (0.143 mL, 1.5 mmol). The reaction mixture was stirred at room temperature overnight, then diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered and evaporated. The residue was purified on Biotage SP-1 eluting with EtOAc/hexane to give the title compound (154 mg, 54%). 1H NMR (400 MHz, DMSO-d6) δ 1.22 (t, J=7.2 Hz, 3H), 2.38 (s, 3H), 2.39 (s, 3H), 4.25 (q, J=7.2 Hz, 2H), 7.25-7.21 (m, 2H). MS 284 (MH+)

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified on Biotage
  6. washSP-1 eluting with EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-cffee9e65b4040e19fe7741b538ccefd
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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