Tetrahydrofuran → [3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)phenyl][2-(morpholin-4-yl)pyrimidin-5-yl]methanol

関与物質

役割	名称	HCID	仕込み量
反応物	Tetrahydrofuran	HCID 8028	—
反応物	2-(Morpholin-4-yl)pyrimidine-5-carbaldehyde	HCID 3160978	—
反応物	1-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene	HCID 22033147	—
反応物	HCID 178418244	HCID 178418244	—
溶媒	Water	HCID 962	—
溶媒	Ethyl Acetate	HCID 8857	—
生成物	[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)phenyl][2-(morpholin-4-yl)pyrimidin-5-yl]methanol	HCID 86686212	85%

反応条件

温度	-78 °C

反応手順

[(3-Bromobenzyl)oxy](tert-butyl)dimethylsilane (860 mg) was mixed with THF (10 ml), followed by cooling to −78° C. under argon atmosphere. A 1.60M n-butyl lithium/hexane solution (1.8 ml) was added dropwise thereto, followed by stirring at −78° C. for 10 minutes, and then 2-morpholin-4-ylpyrimidine-5-carboaldehyde (500 mg) was added thereto. The mixture was warmed to 0° C. over 1 hour and then stirred again at 0° C. for 1 hour. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain [3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl][2-(morpholin-4-yl)pyrimidin-5-yl]methanol (914 mg).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09051283B2
出典データセット	uspto-grants-2015_06
ORD ID	ord-052ef783d09147179497a9afc818aad1
出典メモ	uspto-grants-2015_06