Ethyl Acrylate → HCID 178471088, compound

HRID 472213Notes

Reaction equation

HRID 472213 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[C:5](Br)=[C:4]([CH3:17])[N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:40]([O:44][CH2:45][CH3:46])(=[O:43])[CH:41]=[CH2:42]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[C:5](/[CH:42]=[CH:41]/[C:40]([O:44][CH2:45][CH3:46])=[O:43])=[C:4]([CH3:17])[N:3]=1

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 178433367HCID 178433367, compound

Product 1

HCID 178471088HCID 178471088, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
130 °C

Procedure

A sealed tube containing trans-4-(2-amino-5-bromo-6-methylpyrimidin-4-ylamino)cyclohexanol (655 mg, 2.17 mmol), tri-o-tolylphosphine (298 mg, 0.979 mmol), ethyl acrylate (355 uL, 3.26 mmol) and palladium (II) acetate (73 mg, 0.33 mmol) in triethylamine (20 mL) was evacuated and back-filled with nitrogen (3×). The reaction mixture was heated overnight at 130° C., filtered and concentrated. The residue was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0.5-5%) to afford the title compound (364 mg, 52%).

Workup

  1. customwas evacuated
  2. additionback-filled with nitrogen (3×)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with chloroform/7 N ammonia in methanol (0.5-5%)

Sources & evidence

ORD record
ord-2e4e35fcf5f94f3eb597060023aef19a
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

Loading…