Guanidine Hydrochloride → 5-Amino-3H-thiazolo[4,5]pyrimidine-2-one

HRID 2252410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2252410
Cl[C:2]1[NH:3][C:4](=[O:9])[S:5][C:6]=1[CH:7]=O.Cl.[NH2:11][C:12]([NH2:14])=[NH:13].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:14][C:12]1[N:11]=[CH:7][C:6]2[S:5][C:4](=[O:9])[NH:3][C:2]=2[N:13]=1

Komponenten

6

Edukt 4

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 121980294-Chloro-2-oxo-2,3-dihydro-1,3-thiazole-5-carbaldehyde

Produkt 1

HCID 247640395-Amino-3H-thiazolo[4,5]pyrimidine-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Compound 85 (1.22 g, 7.47 mmol), guanidine hydrochloride (2.13 g, 22.4 mmol), K2CO3 (1.03 g, 7.47 mmol), and NaHCO3 (1.88 g, 22.3 mmol) was suspended in DMF and heated for two days at 110° C. Upon consumption of the starting material as determined by TLC, the solvent was removed under vacuurn. The solid residue was triturated with water. An analytically pure sample of 86 was obtained by HPLC (ODS-A C18; 3-97% CH3CN/H2O gradient; 1.0 mL/min). Tan solid: HPLC Rt=1.63 min; Rf=0.45 (2% H2O, 8% Methanol, 90% Ethyl acetate); 1H NMR (400 MHz, d6-DMSO) δ 8.11 (s, 1H), 6.67 (s, 2H); MS (+)-ES [M+H]+ 169; Elemental analysis for C5H4N4OS.0.1 CH3CN.0.1 H2O: calc'd: C, 35.88; H, 2.61; N, 32.99; S, 18.42. Found: C, 35.96; H, 2.75; N, 32.56; S, 18.42.

Aufarbeitung

  1. customUpon consumption of the starting material
  2. customthe solvent was removed under vacuurn
  3. customThe solid residue was triturated with water

Quellen und Nachweise

ORD-Eintrag
ord-112b4fdd942e49e1970f62537c561cf9
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07321033B2

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