1H-Pyrazol-3-amine, 5-methyl- → HCID 178428230, compound

HRID 1765340Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.CC(C)([O-])C.[Na+].[NH2:25][C:26]1[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)C>[CH3:31][C:29]1[CH:30]=[C:26]([NH:25][C:16]2[CH:17]=[CH:18][C:13]([N:4]3[N:3]=[CH:2][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]3=[O:12])=[CH:14][CH:15]=2)[NH:27][N:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Degassed toluene (6 ml) and ethanol (3 ml) were added in one portion to a mixture of 4-bromo-2-phenyl-2H-phthalazin-1-one (0.750 g, 2.5 mmol), sodium t-butoxide (0.337 g, 3.5 mmol), 3-amino-5-methyl pyrazole (0.291 g, 3 mmol), tris-(dibenzylideneacetone)-dipalladium (0.115 g, 0.125 mmol) and 2-(di-t-butylphosphino)-biphenyl (0.075 g, 0.25 mmol) under nitrogen. The reaction mixture was heated to 100° C. for 20 hours with stirring and then cooled to room temperature. Diethyl ether (10 ml) was added and the precipitated solid was filtered to give the crude product as a grey solid (0.6 g, 76% yield). A 0.06 g portion of the crude product was triturated with acetonitrile (2 ml) and water (2 ml) to give the target compound (0.045 g, 58% yield based on recovered materials). 1H-NMR: (400 MHz, D6-DMSO) 11.96 (1H, s), 9.33 (1H, s), 8.53 (1H, d), 8.38 (1H, d), 7.92–7.99 (2H, m), 7.88 (2H, d), 7.77 (2H, t) 7.34 (1H, t) 6.24 (1H, s) 2.18 (3H, s) MS (ESI+)=(M+H)+ 318.29.

Workup

customDegassed toluene (6 ml) and ethanol (3 ml)
temperaturecooled to room temperature
filtrationthe precipitated solid was filtered

Sources & evidence

ORD record: ord-29f72b6de3bd413d81b52df1ea6fd48d
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226923B2

Reaction notes

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