Dimethylformamide → HCID 118023404, compound

HRID 2171787Notes

Reaction equation

HRID 2171787 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[C:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[S:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.CN(C=O)C.[CH2:23]([O:25]/[CH:26]=[CH:27]/B1OC(C)(C)C(C)(C)O1)[CH3:24].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH:12]1([C:10]2[S:9][C:4]3[N:5]=[C:6]([CH3:8])[N:7]=[C:2](/[CH:24]=[CH:23]/[O:25][CH2:26][CH3:27])[C:3]=3[CH:11]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 219739081-Ethoxyethene-2-boronic acid pinacol esterHCID 118023129HCID 118023129, compound

Product 1

HCID 118023404HCID 118023404, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 4-chloro-6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine (1.0 g) and DMF (40 mL) were added (E)-1-ethoxyethene-2-boronic acid pinacol ester (900 mg) and K3PO4 (4.3 g), and Pd(PPh3)4 (500 mg) was added thereto under an argon atmosphere, followed by heating and stirring at 85° C. for 2 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over Na2SO4, then concentrated under reduced pressure, and purified by silica gel column (hexane/EtOAc) to obtain 6-cyclohexyl-4-[(E)-2-ethoxyvinyl]-2-methylthieno[2,3-d]pyrimidine (885 mg).

Workup

  1. additionwas added
  2. temperatureby heating
  3. extractionfollowed by extraction with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-d5951a1b0b374a51bd19712fd80436f0
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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