Dimethylformamide → HCID 178428499, compound

HRID 1098241Notes

Reaction equation

Br[C:2]1[C:3]([CH3:18])=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[N:15][C:16]([OH:17])=[C:11]3[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:61][N:62](C=O)C>[C-]#N.[Zn+2].[C-]#N.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]>[OH:17][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:8]([C:4]3[C:3]([CH3:18])=[C:2]([CH:7]=[CH:6][CH:5]=3)[C:61]#[N:62])[N:9]=[CH:10][C:11]=12

Participants

Conditions

Temperature: 160 °C

Procedure

1-(3-bromo-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate AT4) (2 g, 6.55 mmol) and Zinc cyanide (0.693 g, 5.90 mmol) were dissolved in DMF (30 mL)and sealed into a microwave tube. The tube was purged with nitrogen. 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.379 g, 0.66 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.300 g, 0.33 mmol) added. The reaction was heated to 160° C. for 10 minutes in the microwave reactor and cooled to RT. The reaction mixture was filtered and the solid washed with DMF (until the filtrate was colourless) to afford the product (1.340 g, 81%) which was used without further purification. 1H NMR (400 MHz, DMSO) δ 2.19 (3H, s), 7.54 (1H, t), 7.71 (1H, d), 7.94 (1H, d), 8.02 (1H, s), 8.30 (1H, s), 12.32 (1H, s)

Workup

customsealed into a microwave tube
customThe tube was purged with nitrogen
temperaturecooled to RT
filtrationThe reaction mixture was filtered
washthe solid washed with DMF (until the filtrate

Sources & evidence

ORD record: ord-47a566d4d0014e099b68d9b40058b621
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143263B2

Reaction notes

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