Sodium Bicarbonate → 2-(4-(4,6-dimethylpyridin-2-yl)benzyl)-7-isobutyl-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81409Notes

Reaction equation

HRID 81409 reaction equation
[CH2:1]([N:5]1[C:10]2=[N:11][N:12]([CH2:21][C:22]3[CH:27]=[CH:26][C:25](B4OC(C)(C)C(C)(C)O4)=[CH:24][CH:23]=3)[C:13]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:9]2[C:8](=[O:37])[N:7]([CH3:38])[C:6]1=[O:39])[CH:2]([CH3:4])[CH3:3].Br[C:41]1[CH:46]=[C:45]([CH3:47])[CH:44]=[C:43]([CH3:48])[N:42]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:47][C:45]1[CH:44]=[C:43]([CH3:48])[N:42]=[C:41]([C:25]2[CH:24]=[CH:23][C:22]([CH2:21][N:12]3[C:13]([NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[C:9]4[C:10]([N:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[C:6](=[O:39])[N:7]([CH3:38])[C:8]4=[O:37])=[N:11]3)=[CH:27][CH:26]=2)[CH:46]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 149751952-Bromo-4,6-dimethylpyridineHCID 685027217-isobutyl-5-methyl-3-(phenylamino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 426408842-(4-(4,6-dimethylpyridin-2-yl)benzyl)-7-isobutyl-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-isobutyl-5-methyl-3-(phenylamino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (41 mg, 0.077 mmol), 2-bromo-4,6-dimethylpyridine (14.3 mg, 0.077), tetrakis(triphenylphosphine)palladium(0) (3 mg), and 1M NaHCO3 aqueous solution (116 uL) in dioxane (350 μL) was heated at 100° C. for 4 hours, and then cooled to room temperature. The mixture was filtered through a 0.45 μm microfilter, and then purified by a semi-preparative HPLC to give pure product as a white powder. MS (ESI) m/z 509.2 [M+H]+

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered through a 0.45 μm microfilter
  3. custompurified by a semi-preparative HPLC
  4. customto give pure product as a white powder

Sources & evidence

ORD record
ord-1858396a1145426eb777b30caf3b026b
Source dataset
uspto-grants-2014_09
Patent number
US08846693B2

Reaction notes

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