Triphenylphosphine → 9-Acetylamino-5-(2-methanesulfenylpyrimidin-4-yl)pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine

https://huagongshe.com/reaction/2054355

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Lithium Chloride	HCID 433294	—
Reactant	9-Acetylamino-5-Iodopyrido[3',2':4,5]Pyrrolo[1,2-c]Pyrimidine	HCID 11152343	—
Reactant	2-(Methylthio)-4-(trimethylstannyl)pyrimidine	HCID 11266229	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	9-Acetylamino-5-(2-methanesulfenylpyrimidin-4-yl)pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine	HCID 9968273	16.2%

Reaction Steps

A solution of 20a (130 mg, 0.37 mmol), 2-methanesulfenyl-4-trimethylstannylpyrimidine (93 mg, 1.10 mmol), Pd2(dba)3 (76 mg, 0.07 mmol), PPh3 (39 mg, 0.15 mmol), LiCl (47 mg, 1.10 mmol) and CuI (14 mg, 0.07 mmol) in dioxane (10 ml) was refluxed for 1.5 hours. The organic solvent was removed and the oil dissolved in CH2Cl2. The organic solution was extracted four times with 4N HCl and the aqueous solution basified with solid Na2CO3. The aqueous solution was extracted with CH2Cl2. The organic layer was evaporated and purified by flash column chromatography. Elution with CH2Cl2/MeOH (99/1) gave 9-Acetylamino-5-(2-methanesulfenylpyrimidin-4-yl)pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine (21 mg, 16%) as a yellow solid and with CH2Cl2/MeOH (95/5) gave 21 (30 mg, 26%) as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07329666B2
Source dataset	uspto-grants-2008_02
ORD ID	ord-41b154386de7434eb6dedd2a7d7a4aec
Source note	uspto-grants-2008_02