Potassium Carbonate → HCID 178508694, compound

HRID 736636Notes

Reaction equation

HRID 736636 reaction equation
[SH:1][C:2]1[NH:10][C:9]2[C:4](=[N:5][CH:6]=[N:7][C:8]=2[NH2:11])[N:3]=1.Br[C:13]1[C:21]([Br:22])=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[K+].[K+]>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].O1CCOCC1>[Br:22][C:21]1[C:13]([S:1][C:2]2[NH:3][C:4]3[C:9]([N:10]=2)=[C:8]([NH2:11])[N:7]=[CH:6][N:5]=3)=[CH:14][C:15]2[O:19][CH2:18][O:17][C:16]=2[CH:20]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2258145,6-Dibromo-1,3-dioxaindaneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178508691HCID 178508691, compound

Product 1

HCID 178508694HCID 178508694, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To 250 mL flask was charged with 8-mercaptoadenine (2.00 g, 11.98 mmol), 5,6-dibromo-benzo-[1,3]dioxole (6.70 g, 24.0 mmol), Pd2dba3 (0.548 g, 0.599 mmol), Xantphos (0.693 g, 1.20 mmol), K2CO3 (3.31 g, 23.95 mmol), and dry dioxane (25 mL). The resulting mixture was heated at 100° C. for 16 h under nitrogen. After cooling, the reaction mixture was filtered and washed with a 2/2/0.5 mixture of CH2Cl2, EtOAc, and MeOH. The combined filtrates were concentrated in vacuo. The dark brown residue was purified by chromatography on SiO2 (CH2Cl2/EtOAc/MeOH, 2/2/0/5) and subsequent recrystallization from MeOH provided the title compound (1.4 g, 32%). 1H NMR (DMSO-d6) δ 8.08 (s, 1H), 7.38 (s, 1H), 7.23 (s, 1H), 6.12 (s, 2H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washwashed with a 2/2/0.5 mixture of CH2Cl2, EtOAc, and MeOH
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. customThe dark brown residue was purified by chromatography on SiO2 (CH2Cl2/EtOAc/MeOH, 2/2/0/5) and subsequent recrystallization from MeOH

Sources & evidence

ORD record
ord-cd8349957e294ff19778321a08b1df9f
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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