Formamide → 6,7,8,9-tetrahydro-1H-[1]benzofuro[3,2-d]pyrimidin-4-one

HRID 215750

Reaktionsgleichung

Reaktionsgleichung von HRID 215750
C([O:3][C:4]([C:6]1S[C:9]2[CH2:11][CH2:12][CH2:13][CH2:14][C:8]=2[C:7]=1[NH2:15])=O)C.[CH:16]([NH2:18])=O.CC([O-:23])(C)C.[K+]>[NH4+].[Cl-]>[N:15]1[C:7]2[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[O:23][C:6]=2[C:4]([OH:3])=[N:18][CH:16]=1

Komponenten

5

Edukt 3

HCID 713FormamideHCID 312340Ethyl 3-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 1785179296,7,8,9-tetrahydro-1H-[1]benzofuro[3,2-d]pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A 15 mL flask was charged with 3-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid ethyl ester (synthesized by the route described in Example 5, Step A; 0.50 g, 2.4 mmol), formamide (4.8 mL), and KOtBu (95%; 0.56 g, 4.8 mmol) under N2. After heating at 110° C. for 12 h, the mixture was poured over cold satd. aq. NH4Cl (10 mL). Filtration afforded the desired product (0.31 g). MS: No signal. 1H NMR (400 MHz, d6-DMSO) δ ppm 8.00 (s, 1H), 2.74-2.69 (m, 2H), 2.56-2.51 (m, 2H), 1.92-1.81 (m, 2H), 1.79-1.69 (m, 2H).

Aufarbeitung

  1. customsynthesized by the route
  2. additionthe mixture was poured over cold satd
  3. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-e86b1b84cc9049dd9ce49509735a6f85
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193178B2

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