Potassium Phosphate, Tribasic → HCID 118023460, compound

HRID 2171799Notes

Reaction equation

HRID 2171799 reaction equation
Br[C:2]1[S:20][C:5]2[N:6]=[C:7]([CH3:19])[N:8]=[C:9]([CH2:10][N:11]3[CH2:16][CH2:15][S:14](=[O:18])(=[O:17])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH2:36][CH2:35][C:32]3([CH2:34][CH2:33]3)[CH2:31][CH:30]=2)O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[O:17]=[S:14]1(=[O:18])[CH2:15][CH2:16][N:11]([CH2:10][C:9]2[C:4]3[CH:3]=[C:2]([C:29]4[CH2:36][CH2:35][C:32]5([CH2:34][CH2:33]5)[CH2:31][CH:30]=4)[S:20][C:5]=3[N:6]=[C:7]([CH3:19])[N:8]=2)[CH2:12][CH2:13]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 231425414,4,5,5-Tetramethyl-2-(spiro[2.5]oct-5-en-6-yl)-1,3,2-dioxaborolaneHCID 118023391HCID 118023391, compound

Product 1

HCID 118023460HCID 118023460, compoundYield 77.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 6-bromo-4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-2-methylthieno[2,3-d]pyrimidine (200 mg), 4,4,5,5-tetramethyl-2-(spiro[2.5]octa-5-en-6-yl)-1,3,2-dioxaborolane (185 mg), and dioxane (4 mL) were added Pd2dba3 (25 mg), dicyclohexyl (2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (50 mg), K3PO4 (340 mg), and water (200 μL), followed by heating and stirring at 100° C. overnight. The reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with EtOAc. The organic layer was dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by a basic silica gel column (hexane/EtOAc) to obtain 4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-2-methyl-6-(spiro[2.5]octa-5-en-6-yl)thieno[2,3-d]pyrimidine (167 mg).

Workup

  1. temperatureby heating
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionfollowed by extraction with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a basic silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-5e07215abbcc4d6bb45bd628622c9418
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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