Potassium Carbonate → HCID 131735866, compound

HRID 2206640Notes

Reaction equation

HRID 2206640 reaction equation
Br[C:2]1[C:3]([NH:9][C@H:10]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH3:11])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:18]([O:23][CH2:24][CH3:25])(=[O:22])[C:19]#[C:20][CH3:21].[Cl-].[Li+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:5]1[N:6]=[CH:7][C:2]2[C:19]([C:18]([O:23][CH2:24][CH3:25])=[O:22])=[C:20]([CH3:21])[N:9]([C@H:10]([CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH3:11])[C:3]=2[N:4]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 433294Lithium ChlorideHCID 89740313HCID 89740313, compound

Product 1

HCID 131735866HCID 131735866, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (S)-5-bromo-2-chloro-N-(1-(tetrahydro-2H-pyran-4-yl)ethyl)Pyrimidin-4-amine (1.5 g, 4.7 mmol) in DMF (20 mL) was added ethyl but-2-ynoate (1.05 g, 9.4 mmol), lithium chloride (296 mg, 7.05 mmol), palladium(II) acetate (105 mg, 0.47 mmol) and potassium carbonate (1.95 g, 14.1 mmol) at 25° C. under N2. The reaction was stirred at 120° C. for 3 hrs. The mixture was filtered and the crude product was purified by column chromatography on silica gel eluted with petroleum ether: ethyl acetate=30:1 to give (S)-ethyl 2-chloro-6-methyl-7-(1-(tetrahydro-2H-pyran-4-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (270 mg, 16.4%) as a yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe crude product was purified by column chromatography on silica gel
  3. washeluted with petroleum ether

Sources & evidence

ORD record
ord-dfad4ad82ec9412087b81b00d4225f64
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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