Potassium Carbonate → HCID 86705382, compound

HRID 707469Notes

Reaction equation

[O:1]=[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[C:5]2[CH:11]=[C:12]([CH:14]=[O:15])[S:13][C:4]=2[NH:3]1.Cl[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:3]2[C:4]3[S:13][C:12]([CH:14]=[O:15])=[CH:11][C:5]=3[C:6]3=[CH:10][CH:9]=[N:8][N:7]3[C:2]2=[O:1])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-Oxo-4,5-dihydropyrazolo[1,5-c]thieno[3,2-e]pyrimidine-2-carbaldehyde (30 mg, 0.14 mmol) was dissolved in N,N-dimethylformamide (3.0 mL), 1-(chloromethyl)-4-methoxybenzene (0.04 ml, 0.27 mmol) and potassium carbonate (57 mg, 0.41 mmol) were added and the reaction stirred at 60° C. for 5 h. Reaction poured into saturated ammonium chloride solution (20 mL), extracted with ethyl acetate (3×10 mL), organics washed with saturated ammonium chloride solution (20 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with ethyl acetate in hexanes, to yield 4-(4-methoxybenzyl)-5-oxo-4,5-dihydropyrazolo[1,5-c]thieno[3,2-e]pyrimidine-2-carbaldehyde as a powder (16 mg, 89%). 1H NMR (400 MHz, acetone-d6) δ 3.80 (s, 3H), 5.46 (s, 2H), 6.92-7.00 (m, 3H), 7.51 (d, J=8.66 Hz, 2H), 8.08 (d, J=1.76 Hz, 1H), 8.37, (s, 1H), 9.94 (s, 1H).

Workup

customReaction
extractionextracted with ethyl acetate (3×10 mL)
washorganics washed with saturated ammonium chloride solution (20 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography
washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record: ord-15911958f084400e9aa5a979a3807cfa
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175010B2

Reaction notes

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