Triphenylphosphine → HCID 67257649, compound

HRID 1845872Notes

Reaction equation

HRID 1845872 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]([OH:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:4][N:3]=1.[Cl:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OCC1C=CC(Cl)=CC=1)=O)=N\C(OCC1C=CC(Cl)=CC=1)=O>ClCCl>[Si:11]([O:10][CH2:9][CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=1)[O:18][C:21]1[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=1[Cl:19])([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 748142-Chloro-4-fluorophenolHCID 11990352916320-82-6HCID 67257102HCID 67257102, compound

Product 1

HCID 67257649HCID 67257649, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of 1-(2-aminopyrimidin-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol (19) (640 mg), 2-Chloro-4-fluorophenol (696 mg) and triphenylphosphine (1246 mg) in dichloromethane (10 mL) was added a solution of (E)-bis(4-chlorobenzyl) diazene-1,2-dicarboxylate in dichloromethane (20 mL) dropwise. The mixture was stirred at 45° C. overnight before being filtered and the filtrate was applied to a silica column and eluted with 10 to 100% ether in heptane. The product containing fractions were concentrated to afford the title compound (835 mg) as a white solid.

Workup

  1. filtrationbefore being filtered
  2. washeluted with 10 to 100% ether in heptane
  3. additionThe product containing fractions
  4. concentrationwere concentrated

Sources & evidence

ORD record
ord-8d506828c7d749cf8279a394955762da
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

Loading…