3-Formylphenylboronic acid → HCID 86618410, compound

HRID 2262131Notes

Reaction equation

HRID 2262131 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.[CH:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)=[O:19]>C([O-])([O-])=O.[Na+].[Na+].C(#N)C.C(OCC)(=O)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:25]=[C:20]([CH:21]=[CH:22][CH:23]=3)[CH:18]=[O:19])=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 2

HCID 27343563-Formylphenylboronic acidHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618410HCID 86618410, compoundYield 35%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19 (300 mg), 130 mg of 3-formylbenzeneboronic acid and 55 mg of Bis(triphenylphosphine)palladium(II) dichloride in 0.6 mL of 1M Na2CO3 and 0.6 mL of acetonitrile was heated to 100° C. in the microwave reactor for 15 min. The reaction mixture was diluted with ethyl acetate (60 mL), and then washed with H2O (40 mL). The organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by ISCO CombiFlash (0-40% ethyl acetate/hexane) to yield 99 mg of 3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzaldehyde.

Workup

  1. washwashed with H2O (40 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by ISCO CombiFlash (0-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0d58a982f1a84871906e81d3cc9dcf51
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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