Bromomethylcyclopropane → 2-chloro-5-(cyclopropylmethyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Temperature

0 °C

To a round-bottomed flask equipped with a magnetic stirrer was added 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (800 mg, 3.32 mmol), DMSO (5 ml), sodium 2-methylpropan-2-olate (351 mg, 3.66 mmol). The reaction mixture was cooled to 0° C. and (bromomethyl)cyclopropane (0.372 ml, 3.66 mmol) was added in DMSO (1 mL). The reaction was removed from the ice-bath and stirred at 20° C. for 16 hours. The heterogeneous suspension was added to water (10 mL) to give a precipitate, which was collected by filtration, was successively washed with water, a small amount of ethanol and diethyl ether. The collected solid was dried in-vacuo to afford 2-chloro-5-(cyclopropylmethyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (746 mg, 2.53 mmol, 76% yield) as a off white solid. MS [M+H] found 295.

1. customTo a round-bottomed flask equipped with a magnetic stirrer
2. customThe reaction was removed from the ice-bath
3. additionThe heterogeneous suspension was added to water (10 mL)
4. customto give a precipitate, which
5. filtrationwas collected by filtration
6. washwas successively washed with water
7. customThe collected solid was dried in-vacuo

ORD record

ord-561180728f9840ce84008cc3a3c85450

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163755B2