3-Methyluracil → 2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	3-Methyluracil	HCID 79066	—
Edukt	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Edukt	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Edukt	(1R,2R)-2-aminocyclopentan-1-ol hydrochloride	HCID 12886906	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one	HCID 67370916	76,5%

Reaktionsschritte

3-Methyluracil (12.6 mg, 0.1 mmol) was dissolved in 0.5 mL of DMF, and then BOP (71 mg, 0.16 mmol) was added. The mixture was stirred at room temperature for two minutes, then (1R,2R)-(−)-2-hydroxycyclopentylamine hydrochloride salt (22 mg, 0.16 mmol) was added, followed by DBU (51 uL, 3.4 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was purified by a semi-preparative HPLC to give pure product (16 mg, yield 76%). MS (ESI) m/z 210.1 [M+H]+.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08664207B2
Quelldatensatz	uspto-grants-2014_03
ORD ID	ord-b91a2c85966e4a2ba3dd38e25348a084
Quellennotiz	uspto-grants-2014_03