6-(2-(dimethylamino)vinyl)-1-methyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrimidine-2,4(1H,3H)-dione → 3-(1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

HRID 60355Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]1[N:10]([CH3:11])[C:9](=[O:12])[N:8]([CH2:13][CH2:14][CH2:15][O:16][CH:17]2[CH2:22]CCC[O:18]2)[C:7](=[O:23])[C:6]=1[N+:24]([O-])=O>CC(O)=O.O.[Zn]>[C:17]([O:16][CH2:15][CH2:14][CH2:13][N:8]1[C:7](=[O:23])[C:6]2[NH:24][CH:3]=[CH:4][C:5]=2[N:10]([CH3:11])[C:9]1=[O:12])(=[O:18])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-(2-(dimethylamino)vinyl)-1-methyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrimidine-2,4(1H,3H)-dione (530 mg, 1.4 mmol) in HOAc (5 mL) was added Zn dust (910 mg, 14 mmol). The reaction was heated at 100° C. for 2 h, cooled to RT, diluted with water (10 mL) and extracted with EA (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (1:1) to give 3-(1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (210 mg, 56% yield) as a white solid. LCMS: MH+ 266 and TR=0.646 min.

Workup

temperaturecooled to RT
extractionextracted with EA (3×20 mL)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated to a residue which
customwas purified by chromatography
washeluted with PE/EA (1:1)

Sources & evidence

ORD record: ord-0b9200a27d2a470b806a7845d3931a13
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440983B2

Reaction notes

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