Phenyl Isothiocyanate → 7-Isobutyl-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81407

Reaction equation

[C:1]1([N:7]=[C:8]=S)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:10]([C:12]1[N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:16](=[O:22])[N:15]([CH3:23])[C:14](=[O:24])[CH:13]=1)[NH2:11]>CN(C=O)C>[CH2:18]([N:17]1[C:12]2=[N:10][NH:11][C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:13]2[C:14](=[O:24])[N:15]([CH3:23])[C:16]1=[O:22])[CH:19]([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 120 °C

Procedure

Phenyl isothiocyanate (0.17 mL, 1.4 mmol) is added to a solution of 6-hydrazinyl-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione (31 mg, 0.47 mmol) in DMF (10 mL). The reaction mixture is heated at 120° C. for 6 hours, and then evaporated to remove solvent under reduced pressure. The residue is further purified by silica-gel flash chromatography to give 20 mg of product (Yield: 41%). 1H NMR (400 MHz, DMSO-d6) δ0.95 (s, 3H), 0.97 (s, 3H), 2.30 (m, 1H), 3.37 (s, 3H), 3.77 (d, 2H), 7.16-7.43 (m, 5H), 7.61 (s, 1H). MS (FAB) m/z 314.3 [M+H]+.

Workup

customevaporated
customto remove solvent under reduced pressure
customThe residue is further purified by silica-gel flash chromatography

Sources & evidence

ORD record: ord-15d73fd7460a4f2aaac3477c717cc714
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846693B2

Linked notes

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