HCID 58075838, compound → HCID 58075657, compound

HRID 2370222Notes

Reaction equation

HRID 2370222 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([OH:12])[CH2:9]C=C)[C:5]([CH:19]=[CH2:20])=[C:4]([NH:21][CH3:22])[N:3]=1>C1C=CC=CC=1.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][CH3:22])[C:5]2[CH:19]=[CH:20][CH2:9][C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([OH:12])[C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 58075838HCID 58075838, compound

Product 1

HCID 58075657HCID 58075657, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1-(2-chloro-6-(methylamino)-5-vinylpyrimidin-4-yl)-1-phenylbut-3-en-1-ol (60 mg) in benzene (5 mL) was added Grubbs I (16 mg), and the reaction mixture was heated at 85° C. for 1 h. The solvent was removed, and the residue was purified by preparative TLC eluting with 40% EtOAc/Hexanes to give the title compound as a colorless oil (50 mg). 1H NMR (500 MHz, CDCl3) δ ppm 7.4 (5H, m), 6.25 (1H, m), 6.07 (1H, m), 5.14 (1H, br. S), 4.52 (1H, s), 3.10 (3H, d<J=5.0 Hz), 2.99 (2H, m). 13C NMR (125 MHz, CDCl3) 164.32, 159.38, 158.85, 144.15, 128.24, 128.02, 127.83, 125.51, 117.54, 108.14, 60.51, 38.50, and 28.57. HRMS calcd. for C15H15ClN3O (M+H) 288.0904; found: 288.0899.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative TLC
  3. washeluting with 40% EtOAc/Hexanes

Sources & evidence

ORD record
ord-96a98302f41644d79a61f6c57e448c38
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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