Tetrahydrofuran → HCID 68880358, compound

Temperature

-10 °C

A solution of sodium bis(trimethylsilyl)amide (1.10 ml) in tetrahydrofuran (1.0M, 1.10 mmol) was added to a suspension of 5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl-amine (0.139 g) and 4-chloro-7-(3-morpholin-4-ylpropoxy)-5-(tetrahydro-2H-pyran-4-yloxy)quinazoline (0.223 g) in DMF (5 ml) that had been cooled to −10° C. and the mixture was stirred for 90 minutes then the reaction was allowed to warm to room temperature and stirred for a further 2 hours. The reaction mixture was quenched into water and saturated ammonium chloride solution was added. This was then extracted into dichloromethane and the organic portion was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of dichloromethane and methanol as eluent. The product material gathered after chromatography as a foam was triturated with diethyl ether and air-dried giving an off-white solid. There was thus obtained the title compound (0.216 g) as a grey solid;

1. temperatureto warm to room temperature
2. stirringstirred for a further 2 hours
3. customThe reaction mixture was quenched into water and saturated ammonium chloride solution
4. additionwas added
5. extractionThis was then extracted into dichloromethane
6. washthe organic portion was washed with brine
7. dry with materialdried over magnesium sulfate
8. customevaporated
9. customThe residue was purified by column chromatography on silica using
10. temperatureincreasingly polar mixtures of dichloromethane and methanol as eluent
11. customwas triturated with diethyl ether
12. customair-dried
13. customgiving an off-white solid

ORD record

ord-a5cbadec675348bd8b6d4b2d2eed6ed8

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504408B2