Sodium Hydroxide → 2-Butyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

Reaction equation

P(Cl)(Cl)([Cl:3])=O.[CH2:6]([C:10]1[NH:11][C:12](=O)[C:13]2[NH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH2:7][CH2:8][CH3:9].[OH-].[Na+]>>[CH2:6]([C:10]1[N:11]=[C:12]([Cl:3])[C:13]2[NH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH2:7][CH2:8][CH3:9]

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 1370052332-Butyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

Product 1

HCID 1183828482-Butyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidineYield 91.2%

Procedure

Phosphorus oxychloride (20 mL, 21.46 mmol) was added to 2-butyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (1.69 g). The resultant mixture was heated at 100° C. After 4 hours the reaction mixture was cooled to room temperature then poured onto ice. The aqueous phase was treated with aqueous sodium hydroxide solution (5M) until the pH was 7. The resultant mixture was extracted with ethyl acetate (2×150 mL). The combined organic phase were washed with brine, dried (Na2SO4), filtered and evaporated to give the title compound (1.69 g)