3,5-Dimethylpyrazole → HCID 71285741, compound

HRID 536511Notes

Reaction equation

[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[C:16](I)[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)=[N:6]1.[CH3:31][C:32]1[CH:36]=[C:35]([CH3:37])[NH:34][N:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+].OC1C=CC=CC=1C=NO>C(#N)C.[Cu-]=O>[CH3:31][C:32]1[CH:36]=[C:35]([CH3:37])[N:34]([C:16]2[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=[C:14]([C:7]3[C:8]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[N:5]([CH2:4][C:3]4[CH:27]=[CH:28][CH:29]=[CH:30][C:2]=4[F:1])[N:6]=3)[N:15]=2)[N:33]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Under argon atmosphere, 150 mg (purity 62%, 0.18 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (example 15A) was suspended in 2 ml of absolute acetonitrile, and 26 mg (0.27 mmol) of 3,5-dimethyl-1H-pyrazole, 118 mg (0.36 mmol) of caesium carbonate, 5 mg (0.04 mmol) of copper(I) oxide and 20 mg (0.15 mmol) of 2-hydroxybenzaldehyde-oxime were added. The mixture was heated in the microwave for 1 h at 150° C. Then 346 mg (3.62 mmol) of 3,5-dimethyl-1H-pyrazole was added and the mixture was heated in the microwave for 45 min at 200° C. The reaction solution was filtered and purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0). 20 mg (23% of theor.) of the target compound was obtained.

Workup

temperaturethe mixture was heated in the microwave for 45 min at 200° C
filtrationThe reaction solution was filtered
custompurified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0)
custom20 mg (23% of theor.) of the target compound was obtained

Sources & evidence

ORD record: ord-b40f95e53dbe472e94e3c07e0d2f3f76
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859569B2

Reaction notes

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