Sodium Carbonate → HCID 135984709, compound

HRID 249789Notes

Reaction equation

HRID 249789 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]2[N:19]=[C:18]3[N:10]([C:11](=[O:24])[N:12]([CH2:20][CH2:21][CH2:22][CH3:23])[C:13]4[N:14]=[CH:15][NH:16][C:17]=43)[N:9]=2)=[CH:4][CH:3]=1.[N:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.CCOC(C)=O.Br[Pd](Br)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:20]([N:12]1[C:13]2[N:14]=[CH:15][NH:16][C:17]=2[C:18]2=[N:19][C:8]([CH2:7][O:6][C:5]3[CH:25]=[CH:26][C:2]([C:30]4[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=4)=[CH:3][CH:4]=3)=[N:9][N:10]2[C:11]1=[O:24])[CH2:21][CH2:22][CH3:23]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 135984676HCID 135984676, compound

Product 1

HCID 135984709HCID 135984709, compoundYield 30.1%

Reagents, catalysts & solvents 4

HCID 178419754HCID 178419754, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

8-[(4-bromophenoxy)methyl]-4-butyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one (100 mg, 0.24 mmol) and 4-pyridinylboronic acid (32 mg, 0.26 mol) were dissolved in N,N-dimethylformamide (3 mL) in a microwave tube. After the solution was degassed with N2 for 5 minutes, dibromo[bis(triphenylphosphoranyl)]-palladium (20 mg, 0.02 mmol) and a solution of sodium carbonate in water (2 M, 1 mL) were added. The reaction mixture was heated on a microwave reactor at 120° C. for 20 minutes. After cooling down to room temperature, the reaction mixture was diluted with water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were concentrated. The residue was dissolved in DMSO/acetonitrile and purified by preparative LCMS (method A) to yield the desired product as white powder (30 mg, 24% yield). LCMS calculated for C22H22N7O2 (M+H): 416.2. found: 417.1.

Workup

  1. customAfter the solution was degassed with N2 for 5 minutes
  2. temperatureAfter cooling down to room temperature
  3. extractionThe aqueous layer was extracted with EtOAc
  4. concentrationThe combined organic layers were concentrated
  5. dissolutionThe residue was dissolved in DMSO/acetonitrile
  6. custompurified by preparative LCMS (method A)

Sources & evidence

ORD record
ord-4a6ef9b3caec46bbaf533ddaf198c6c1
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

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