Dimethylformamide → 2-(4-(6-fluoropyridin-2-yl)benzyl)-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 57654Notes

Reaction equation

[F:1][C:2]1[N:7]=[C:6]([C:8]2[CH:26]=[CH:25][C:11]([CH2:12][N:13]3[CH:21]=[C:20]4[C:15]([NH:16][C:17](=[O:24])[N:18]([CH3:23])[C:19]4=[O:22])=[N:14]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:27](I)[CH:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:1][C:2]1[N:7]=[C:6]([C:8]2[CH:26]=[CH:25][C:11]([CH2:12][N:13]3[CH:21]=[C:20]4[C:15]([N:16]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:17](=[O:24])[N:18]([CH3:23])[C:19]4=[O:22])=[N:14]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

2-(4-(6-fluoropyridin-2-yl)benzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (422 mg, 1.2 mmol), isobutyl iodide (276 μL, 2.4 mmol) and potassium carbonate (497 mg, 3.6 mmol) are place in a Biotage microwave vial, and then DMF (6 mL) is added. The mixture is heated in a Biotage microwave instrument at 140° C. for 30 min. The mixture is diluted with water (150 mL), and then extracted with methylene chloride three times. The combined organic phase is evaporated to dryness to give 460 mg of crude product as pale yellow solids, which is used in the next step without further purification. MS (ESI) m/z 408.2 [M+H]+.

Workup

extractionextracted with methylene chloride three times
customThe combined organic phase is evaporated to dryness

Sources & evidence

ORD record: ord-9ba5da0832a2484395d1aaa125a598f2
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434730B2

Reaction notes

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