Ethyl Acrylate → HCID 178471090, compound

HRID 2390018Notes

Reaction equation

HRID 2390018 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]2)[C:5](Br)=[C:4]([CH3:20])[N:3]=1.[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[CH2:23]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@@H:12]([O:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]2)[C:5](/[CH:23]=[CH:22]/[C:21]([O:25][CH2:26][CH3:27])=[O:24])=[C:4]([CH3:20])[N:3]=1

Participants

5

Reactant 2

HCID 8821Ethyl AcrylateHCID 178433368HCID 178433368, compound

Product 1

HCID 178471090HCID 178471090, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
130 °C

Procedure

In a sealed tube a solution of 2-(cis-4-(2-amino-5-bromo-6-methylpyrimidin-4-ylamino)cyclohexyloxy)ethanol (695 mg, 4.03 mmol) and ethyl acrylate (438 uL, 4.03 mmol) in triethylamine (10 mL) was bubbled with argon for ˜5 minutes. Tetrakis(triphenylphosphin)-palladium (0) (232 mg, 0.201 mmol) was added, the vial was sealed and the mixture was bubbled again with argon (5 minutes). The reaction was heated to 130° C. overnight, cooled to room temperature and concentrated. The residue was dissolved in chloroform (500 mL) and washed with water and brine, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0-4%) to afford the title compound (615 mg, 84%).

Workup

  1. customthe vial was sealed
  2. customthe mixture was bubbled again with argon (5 minutes)
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in chloroform (500 mL)
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography
  11. washeluting with chloroform/7 N ammonia in methanol (0-4%)

Sources & evidence

ORD record
ord-54de913eb59448889722d3e18f571e58
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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