Dimethylformamide → 5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Dichloromethane	HCID 6344	—
Reactant	Lithium diisopropylamide	HCID 2724682	—
Reactant	4-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine	HCID 57685385	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Tetrahydrofuran heptane ethylbenzol	HCID 22742125	—
Product	5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde	HCID 57685405	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine was slurried in tetrahydrofuran and cooled to −78° C. under nitrogen. Two equivalents of 2M lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene was added slowly and the solution was stirred for 30 minutes, dimethylformamide (6 eq) was added and the solution was stirred at −78° C. for an additional one hour. The solution was warmed to 0° C. and ice cold 0.1N hydrochloric acid was added and the solution was warmed to room temperature before extraction with methylene chloride. The organic layer was dried with sodium sulfate and concentrated to give 5-chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08158626B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-bb80011775b74f64b34715223ffa897d
Source note	uspto-grants-2012_04