Triethylamine → 3-Chloro-1-(2,2-dimethyl-morpholin-4-yl)-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b,9-tetraaza-fluorene

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2,2-Dimethylmorpholine	HCID 18959674	—
Reactant	2,4-Dichloro-6,6-dimethyl-8,9-dihydro-6H-[1,4]oxazino[4,3-e]purine	HCID 86667371	—
Product	3-Chloro-1-(2,2-dimethyl-morpholin-4-yl)-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b,9-tetraaza-fluorene	HCID 86667373	85.4%

Reaction Conditions

Temperature	140 °C

Reaction Steps

A mixture of 1,3-dichloro-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b,9-tetraaza-fluorene (100 mg, 0.366 mmol), 2,2-dimethyl-morpholine (84 mg, 0.732 mmol) and triethylamine (77 μL, 0.55 mmol) in IMS (2 mL) was heated at 140° C. for 20 mins in a microwave reactor, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 10% ethyl acetate in cyclohexane) affording 3-Chloro-1-(2,2-dimethyl-morpholin-4-yl)-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b,9-tetraaza-fluorene as a white solid (110 mg, 85%). LCMS (method A): RT=3.51 min, [M+H]+=352.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883799B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-99013a31539c4c7aa296464e38953986
Source note	uspto-grants-2014_11