Potassium Carbonate → HCID 178433707, compound

HRID 487288Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][CH:3]([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)=[N:13][C:14](N)=[C:9]3[C:8]([CH3:22])=[N:7]2)[CH2:2]1.N([O-])=[O:24].[Na+].C([O-])([O-])=O.[K+].[K+]>S(=O)(=O)(O)O.O>[O:1]1[CH2:5][CH2:4][CH:3]([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)=[N:13][C:14](=[O:24])[C:9]3=[C:8]([CH3:22])[NH:7]2)[CH2:2]1

Participants

Conditions

Temperature: -5 °C

Procedure

To a solution of 1-(3-tetrahydrofuranyl)-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine (1.08 g, 3.6 mmol) in 60% sulfuric acid (30 ml) at -10° C. was added sodium nitrite (5.6 g, 81.2 mmol) in water (8 ml). The reaction mixture was stirred at -5° C. for 2 hours, then at room temperature for 24 hours. The mixture was poured onto ice-water, neutralized with K2CO3 and the salts were collected by filtration. The aqueous filtrate was extracted with chloroform (6×100 ml) and the combined organic layers were concentrated in vacuo. The residue was dissolved in isopropanol, treated with Darco and concentrated in vacuo to afford 0.5 g (46%) of 1-(3-tetrahydrofuranyl)-3-methyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one.1/4 hydrate as an off-white fluffy powder, m.p. 251° C. when dried at 90° C. for 24 hours in high vacuum.

Workup

waitat room temperature for 24 hours
additionThe mixture was poured onto ice-water
filtrationthe salts were collected by filtration
extractionThe aqueous filtrate was extracted with chloroform (6×100 ml)
concentrationthe combined organic layers were concentrated in vacuo
dissolutionThe residue was dissolved in isopropanol
additiontreated with Darco
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f6ba8b3836d34d79a899ef5b5f46f105
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05294612

Reaction notes

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