Water → 2-Amino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3h)-one

HRID 2167926

Reaktionsgleichung

[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].ClC1C=CC=C2C=1C1C(=O)NC(NC(=O)C(C)(C)C)=[N:26][C:20]=1[NH:21]2.O.[OH-].[NH4+]>CS(C)(=O)=O>[NH2:21][C:20]1[NH:26][C:7](=[O:8])[C:6]2[C:5]3[CH2:12][CH2:13][CH2:14][CH2:15][C:4]=3[S:3][C:2]=2[N:1]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a 50 mL flask was added 4 (225 mg, 1 mmol), 9 (452 mg, 4 mmol) in DMSO2 (500 mg) was heated at 150° C. for 2 h. The mixture was cooled to room temperature. 15 mL water was added and ammonium hydroxide was used to neutralize the suspension. The brown solid was obtained by filtration. Washed with water and dried. The solid was dissolved in methanol and silica gel was added. A dry silica gel plug obtained after evaporation. The plug was then loaded on the column and washed with 5% methanol in chloroform. The fractions containing the desired product (TLC) were pooled and evaporated to afford 132 mg (60%) of 10 as a white solid: 1H NMR (DMSO-d6) δ 1.71 (m, 4H), 2.60 (m, 2H), 2.72 (m, 2H), 6.38 (s, 2H), 10.72 (s, 1H). Anal. calcd for C10H11N3OS: C, 54.28; H, 5.01; N, 18.99; 0, 7.23; S, 14.49. Found: C, 53.45; H, 5.06; N, 18.26; S, 14.02.

Aufarbeitung

temperatureThe mixture was cooled to room temperature
customThe brown solid was obtained by filtration
washWashed with water
customdried
dissolutionThe solid was dissolved in methanol
additionsilica gel was added
customA dry silica gel plug obtained
customafter evaporation
washwashed with 5% methanol in chloroform
additionThe fractions containing the desired product (TLC)
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-9670d658b64e4efea1b827f92515735d
Quelldatensatz: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09045489B2

Verknüpfte Notizen

Wird geladen…