Water → 5-(4-Nitrophenyl)thieno[2,3-d]pyrimidine-2,4-diamine

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=O)=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8].Cl.Cl[C:20]([NH2:22])=[NH:21].[OH2:23]>COCCOCCOC>[N+:15]([C:12]1[CH:11]=[CH:10][C:9]([C:5]2[C:6]3[C:7]([NH2:8])=[N:21][C:20]([NH2:22])=[N:1][C:2]=3[S:3][CH:4]=2)=[CH:14][CH:13]=1)([O-:17])=[O:23]

Participants

Procedure

A suspension of Example 58B (1 g, 4.08 mmol) and chloroformamidine hydrochloride (1.17 g, 10.2 mmol) in diglyme (40 mL) was heated to 130° C. for 15 hours. The mixture was cooled to room temperature, diluted with water, and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was further concentrated under a stream of nitrogen, and purified by silica gel chromatography with 5 to 7% methanol/dichloromethane to provide 0.26 g of the desired product. MS (ESI(+)) m/e 288 (M+H)+.