Phosphorus oxychloride → HCID 69194592, compound

HRID 2389521Notes

Reaction equation

[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([NH:11][C:12](=O)[N:13]([CH3:18])[C:14]3=[O:17])=[N:9]2)=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:28]>>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([N:11]=[C:12]([Cl:28])[N:13]([CH3:18])[C:14]3=[O:17])=[N:9]2)=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 136339895HCID 136339895, compound

Product 1

HCID 69194592HCID 69194592, compoundYield 98.5%

Procedure

2-(biphenyl-4-ylmethyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (25 mg, 0.075 mmol) is refluxed in POCl3 (10 mL) for 60 hours, and the mixture is evaporated to dryness. The residue is purified by silica gel flash chromatography to give 26 mg product as white solids (Yield: 98.5%). 1H NMR (400 MHz, CDCl3) δ 3.68 (s, 3H), 5.45 (s, 2H), 7.39 (m, 3H), 7.43 (m, 2H), 7.59 (m, 4H), 8.01 (s, 1H). MS (FAB) m/z 351.2 [M+H]+.

Workup

customthe mixture is evaporated to dryness
customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-52c2d5e896a54721afe2f6ce0a183321
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273750B2

Reaction notes

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