Diisopropylethylamine → HCID 89996004, compound

HRID 1480861Notes

Reaction equation

HRID 1480861 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[C:12](Br)=[CH:11][N:10]=[C:9]([S:14][CH3:15])[N:8]=1)=[O:6])[CH:2]=[CH2:3].C(N(C(C)C)CC)(C)C>CC(N(C)C)=O.C(Cl)Cl>[CH3:3][C:2]1[C:12]2[CH:11]=[N:10][C:9]([S:14][CH3:15])=[N:8][C:7]=2[C:5](=[O:6])[NH:4][CH:1]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 89996015HCID 89996015, compound

Product 1

HCID 89996004HCID 89996004, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of N-allyl-5-bromo-2-(methylthio)pyrimidine-4-carboxamide (Preparation 187, 24 mg, 0.083 mmol), diisopropylethyl amine (60 μl, 0.344 mmol) and PdCl2dppf.DCM (7 mg, 8.57 μmol) was dissolved in DMA (0.8 mL) and heated to 120° C. for 18 hours. Additional batches of base (60 uL) and catalyst (7 mg) were added and the mixture stirred at 150° C. for 8 hours. The mixture was diluted with DCM and quenched with brine. The aqueous layer was extracted with DCM and the combined organic layers washed with water, dried and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0 to 5% MeOH in DCM to give the title compound (8 mg, 47%).

Workup

  1. customquenched with brine
  2. extractionThe aqueous layer was extracted with DCM
  3. washthe combined organic layers washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 0 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-670efb6fca05408abd61455f022de5b5
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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