(3-Methoxyphenyl)boronic acid → HCID 86618434, compound

HRID 2098792Notes

Reaction equation

HRID 2098792 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)=[CH:8][C:6]=2[N:7]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1>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:24]3[CH:23]=[CH:22][CH:21]=[C:20]([O:19][CH3:18])[CH:25]=3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618434HCID 86618434, compoundYield 66.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19 (150 mg), 66 mg of 3-methoxyphenylboronic acid and 14 mg of bis(triphenylphosphine)palladium(II) dichloride in 1 mL of 1M Na2CO3 aqueous solution and 1 mL of acetonitrile was heated to 100° C. in a sealed microwave reactor for 20 min. The reaction mixture was evaporated. The crude product was purified by flash chromatography eluting with 0-50% EtOAc/hexane to yield 2-chloro-6-(3-methoxyphenyl)-4-morpholinothieno[3,2-d]pyrimidine (94 mg, 66%).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe crude product was purified by flash chromatography
  3. washeluting with 0-50% EtOAc/hexane

Sources & evidence

ORD record
ord-9ca996e2fc8d462981f69333f9e658f2
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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