Ethyl Acetate → HCID 86618410, compound

HRID 2098707Notes

Reaction equation

HRID 2098707 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.C([O:21][CH2:22][CH3:23])(=O)C>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:5]3[CH:4]=[C:23]([CH:9]=[CH:8][CH:6]=3)[CH:22]=[O:21])=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618410HCID 86618410, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19 (300 mg), 130 mg of 3-formylbenzenelboronic 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-9e3ab9bc2e484fdab11fc3eac7e4a71e
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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