Ethyl Acrylate → HCID 178471089, compound

HRID 641677Notes

Reaction equation

HRID 641677 reaction equation
Br[C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([O:17][CH3:18])[CH2:13][CH2:12]2)=[N:4][C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21]>C(N(CC)CC)C.C(OCC)(=O)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]>[NH2:9][C:5]1[N:4]=[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([O:17][CH3:18])[CH2:13][CH2:12]2)[C:2](/[CH:21]=[CH:20]/[C:19]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]([CH3:8])[N:6]=1

Participants

6

Reactant 2

HCID 8821Ethyl AcrylateHCID 178496607HCID 178496607, compound

Product 1

HCID 178471089HCID 178471089, compoundYield 78.4%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

In a sealed tube a solution of 5-bromo-N4-(trans-4-methoxycyclohexyl)-6-methylpyrimidine-2,4-diamine (811 mg, 2.57 mmol) and ethyl acrylate (559 uL, 5.15 mmol) in triethylamine (25 mL) was bubbled with argon for ˜10 minutes. Tetrakis(triphenylphosphin)-palladium (0) (297 mg, 0.257 mmol) was added, the vial was sealed, and the reaction was heated to 130° C. overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (450 mL), washed with water, 0.1 N hydrochloric acid, brine, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with chloroform/methanol (0-10%) to afford (E)-ethyl 3-(2-amino-4-(trans-4-methoxycyclohexylamino)-6-methylpyrimidin-5-yl)acrylate (674 mg, 78%).

Workup

  1. customthe vial was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with water, 0.1 N hydrochloric acid, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washeluting with chloroform/methanol (0-10%)

Sources & evidence

ORD record
ord-fc9d43ec0e9c491cad398f65cf6aba7c
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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