Sodium Hydroxide → 3-(2-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-1-methylpropoxy)propionic acid tert.-butyl ester

HRID 1926947Notes

Reaction equation

HRID 1926947 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:18]([O:20][CH:21]([CH3:25])[CH:22]([OH:24])[CH3:23])=[N:17][CH:16]=[N:15][C:14]=3[O:13][C:12]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:7][CH:6]=1.[C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:35])[CH:33]=[CH2:34]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:37]([O:36][C:32](=[O:35])[CH2:33][CH2:34][O:24][CH:22]([CH3:23])[CH:21]([O:20][C:18]1[C:19]2[C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=3)=[C:12]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:13][C:14]=2[N:15]=[CH:16][N:17]=1)[CH3:25])([CH3:40])([CH3:39])[CH3:38]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15458tert-Butyl acrylateHCID 580169433-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}butan-2-ol

Product 1

HCID 250964163-(2-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-1-methylpropoxy)propionic acid tert.-butyl ester

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Add 2.2 ml of 45% sodium hydroxide solution to a mixture of 900 mg (2.31 mmol) 3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}butan-2-ol, 1477 mg (11.53 mmol) tert.-butyl acrylate and 157 mg (0.46 mmol) tetra-n-butylammonium hydrogensulphate in 10 ml dichloromethane at 0° C., and stir at this temperature for one hour. After a further 16 hours at room temperature, filter the reaction mixture, and concentrate the filtrate by vacuum evaporation. Purify the raw product by preparative RP-HPLC (gradient: water/acetonitrile). 690 mg (57% of theor.) of the desired product is obtained as (R,S/S,R) racemate.

Workup

  1. waitAfter a further 16 hours at room temperature
  2. filtrationfilter the reaction mixture
  3. concentrationconcentrate the filtrate
  4. customby vacuum evaporation
  5. customPurify the raw product by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-d0e9b9bd6a1e420788e706936d9bdaf5
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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