Methanol, 1,1-diethoxy-, 1-acetate → 2,6-dichloro-9-cyclobutyl-9H-purine

HRID 928187Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:12][CH2:11][CH2:10]2)[C:5]([NH2:13])=[C:4]([Cl:14])[N:3]=1.[C:15](OC(OCC)OCC)(=O)C>CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]2[C:5]([N:13]=[CH:15][N:8]2[CH:9]2[CH2:10][CH2:11][CH2:12]2)=[C:4]([Cl:14])[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2,6-Dichloro-N4-cyclobutylpyrimidine-4,5-diamine (crude, 5.65 mmol) in diethoxymethyl acetate (8 mL) was stirred and heated at 80° C. for 16 hr. The mixture was cooled to rt, diluted with EtOAc (80 mL) and washed with water (80 mL), sat. NaHCO3 (80 mL) and brine (80 mL). The organic layer was dried over Na2SO4 and concentrated. The crude product was purified via flash chromatography eluting with 20-50% EtOAc/heptanes to give the title compound as an off-white solid (727 mg, 53% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.95 (1 H, s) 5.07 (1 H, quin, J=8.56 Hz) 2.59-2.77 (2 H, m) 2.42-2.50 (2 H, m) 1.71-1.96 (2 H, m); m/z (APCI+) for C9H8Cl2N4 243.10 (M+H)+.

Workup

temperatureThe mixture was cooled to rt
washwashed with water (80 mL), sat. NaHCO3 (80 mL) and brine (80 mL)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customThe crude product was purified via flash chromatography
washeluting with 20-50% EtOAc/heptanes

Sources & evidence

ORD record: ord-1530192d49864017867d49e4d763ddb1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290496B2

Reaction notes

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