Phenol → HCID 54760677, compound

HRID 57657Notes

Reaction equation

HRID 57657 reaction equation
Cl[C:2]1[N:3]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[N:26]=3)=[CH:21][CH:20]=2)[N:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[C:38]1([OH:44])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O1CCOCC1>CN(C=O)C>[F:31][C:27]1[N:26]=[C:25]([C:22]2[CH:23]=[CH:24][C:19]([CH2:18][N:3]3[C:2]([O:44][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[C:10]4[C:5]([N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7](=[O:13])[N:8]([CH3:12])[C:9]4=[O:11])=[N:4]3)=[CH:20][CH:21]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 700947733-chloro-2-(4-(6-fluoropyridin-2-yl)benzyl)-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 54760677HCID 54760677, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

3-chloro-2-(4-(6-fluoropyridin-2-yl)benzyl)-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (40 mg, 0.095 mmol), potassium carbonate (40 mg, 0.28 mmol) and phenol (26 mg, 0.28 mmol) are placed in a Biotage microwave vial, and then 0.4 mL of dioxane is added. The vial is sealed, and then heated in a Biotage microwave instrument at 150° C. for 3 h. The reaction mixture is diluted with DMF, and then filtered. The filtrate is purified with a semi-preparative HPLC to give 32 mg of pure product as pale yellow crystals (Purity: 99.9%). MS (ESI) m/z 500.2 [M+H]+.

Workup

  1. customThe vial is sealed
  2. filtrationfiltered
  3. customThe filtrate is purified with a semi-preparative HPLC

Sources & evidence

ORD record
ord-72c39e7582814996954f17d358664568
Source dataset
uspto-grants-2016_09
Patent number
US09434730B2

Reaction notes

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