Phosphorus oxychloride → 2-Amino-4-chloroindolo[2,3-d]pyrimidine hydrochloride
Reaction equation
[NH2:1][CH:2]1[N:7]=[C:6]2[N:8]=[C:9]3[C:14]([CH:13]=[CH:12][CH:11]=[CH:10]3)=[C:5]2[C:4](=O)[NH:3]1.P(Cl)(Cl)([Cl:18])=O>O1CCOCC1>[ClH:18].[NH2:1][C:2]1[N:3]=[C:4]([Cl:18])[C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:6]=2[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of 2-amino-4-oxo-3H-indolo[2,3-d]pyrimidine (490 mg, 2.5 mmol) and phosphoryl chloride (7 ml, 75 mmol) in dioxane (13 ml) is heated under reflux for 4 hr, then concentrated in vacuo. The residue is triturated with ethanol, filtered, and the solids washed with 10:1 Ethanol:Ethyl Acetate to give 170 mg (27%) 2-amino-4-chloroindolo[2,3-d]pyrimidine hydrochloride as a grey solid, mp>250 C.