(3-Acetamidophenyl)boronic acid → HCID 86618443, compound

HRID 2098812Notes

Reaction equation

HRID 2098812 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([I:11])=[CH:8][C:6]=2[N:7]=1.[C:18]([NH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:20])[CH3:19]>C([O-])([O-])=O.[Na+].[Na+].C(#N)C.Cl[Pd](Cl)([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>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([C:26]3[CH:27]=[C:22]([NH:21][C:18](=[O:20])[CH3:19])[CH:23]=[CH:24][CH:25]=3)([I:11])[CH2:8][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 157274(3-Acetamidophenyl)boronic acidHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618443HCID 86618443, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19, 129 mg of 3-acetamidophenylboronic acid (250 mg) and 23 mg of bis(triphenylphosphine)palladium(II) dichloride in 1.5 mL of 1M Na2CO3 aqueous solution and 1.5 mL of acetonitrile was heated to 100° C. in a sealed microwave reactor for 15 min. Upon completion, the reaction mixture was evaporated. The crude product was purified by flash chromatography eluting with 20˜100% EtOAc/hexane to yield N-(3-(2-chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine-6-yl)phenyl)acetamide (530 mg, 53%).

Workup

  1. customUpon completion, the reaction mixture was evaporated
  2. customThe crude product was purified by flash chromatography
  3. washeluting with 20˜100% EtOAc/hexane

Sources & evidence

ORD record
ord-8a4b0259ca864a71b7051a3784225d35
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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