Guanidine Hydrochloride → Methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate

HRID 2175902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175902
CN([CH:4]=[C:5]1[C:9](=O)[CH2:8][CH:7]([C:11]([O:13][CH3:14])=[O:12])[CH2:6]1)C.Cl.[NH2:16][C:17]([NH2:19])=[NH:18].C[O-].[Na+]>CO>[NH2:18][C:17]1[N:19]=[CH:4][C:5]2[CH2:6][CH:7]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:9]=2[N:16]=1

Komponenten

5

Edukt 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 86727100Methyl 3-[(dimethylamino)methylidene]-4-oxocyclopentanecarboxylate

Produkt 1

HCID 86727099Methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of methyl 3-[(dimethylamino)methylidene]-4-oxocyclopentanecarboxylate (71.7 mg, 0.36 mmol) in anhydrous methanol (2.5 mL) was added guanidine hydrochloride (124.7 mg, 1.3 mmol) followed by sodium methoxide in methanol (0.24 mL, 1.27 mmol). The mixture was heated to 90° C. in a sealed tube overnight. The crude reaction was quenched with 2 N HCl and concentrated in vacuo. The aqueous residue was purified by HPLC (30×100 mm Waters Sunfire column; 5 micron; 35 mL/min.; 210 nM; 0% to 40% CH3CN+0.05% TFA/water+0.05% TFA over 15 min.; the compound eluted at 10% CH3CN+0.05% TFA/water+0.05% TFA) to afford the title compound after lyophilization.

Aufarbeitung

  1. customThe crude reaction
  2. customwas quenched with 2 N HCl
  3. concentrationconcentrated in vacuo
  4. customThe aqueous residue was purified by HPLC (30×100 mm Waters Sunfire column
  5. washthe compound eluted at 10% CH3CN+0.05% TFA/water+0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-dee21f97baec43fe97cf9bd7ab342a77
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062070B2

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