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Dimethylformamide → HCID 178428499, compound

HRID 1098241
Notes
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Reaction equation

HRID 1098241 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1784216951-(3-bromo-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol

Product 1

HCID 178428499HCID 178428499, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 11186
Zinc cyanide (Zn(CN)2)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

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

  1. customsealed into a microwave tube
  2. customThe tube was purged with nitrogen
  3. temperaturecooled to RT
  4. filtrationThe reaction mixture was filtered
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes