N,N'-Dimethylethylenediamine → 1-[3-Methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]hexahydropyrimidin-2-one

関与物質

役割	名称	HCID	仕込み量
反応物	N,N'-Dimethylethylenediamine	HCID 8070	—
反応物	Potassium Carbonate	HCID 11430	—
反応物	2(1H)-Pyrimidinone, tetrahydro-	HCID 74615	—
反応物	1-(6-Bromo-5-methoxy-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine	HCID 86707155	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
生成物	1-[3-Methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]hexahydropyrimidin-2-one	HCID 72714759	15.2%

反応条件

温度	110 °C

反応手順

A solution containing 1-(6-bromo-5-methoxy-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine (50 mg, 0.126 mmol), tetrahydro-2-pyrimidinone (40 mg, 0.38 mmol), Copper(I) iodide (126 mg, 0.126 mmol), Potassium carbonate (21 mg, 0.15 mmol) and N,N′-Dimethylethylenediamine (0.028 mL, 0.252 mmol) was stirred at 110° C. 18 h. The reaction was filtered through celite and concentrated. The crude product was submitted for reverse phase HPLC to give 251 (8 mg, 14%). MS (ESI) m/z: 417.1. 1H NMR (400 MHz, DMSO) δ 9.61 (s, 1H), 9.47 (s, 1H), 9.33 (s, 1H), 8.68 (s, 1H), 8.63 (s, 1H), 7.89 (d, J=8.7 Hz, 1H), 7.77 (d, J=8.8 Hz, 1H), 6.74 (s, 1H), 3.86 (s, 3H), 3.35 (d, J=5.4 Hz, 2H), 2.63 (s, 3H), 2.16-2.08 (m, 2H).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09434725B2
出典データセット	uspto-grants-2016_09
ORD ID	ord-ac7e2d53a6244edfa23396fb3a7afb42
出典メモ	uspto-grants-2016_09