Phosphoric acid dibenzyl ester 4-(4-tert-butyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-ylmethyl ester → Phosphoric acid mono-[4-(4-tert-butyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-ylmethyl]ester

HRID 2113614Notes

Reaction equation

HRID 2113614 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=4)=[CH:19][CH:20]=3)[N:15]=[C:14]([CH2:32][O:33][P:34](=[O:51])([O:43]CC3C=CC=CC=3)[O:35]CC3C=CC=CC=3)[N:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=4)=[CH:19][CH:20]=3)[N:15]=[C:14]([CH2:32][O:33][P:34](=[O:35])([OH:43])[OH:51])[N:13]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 9987362Phosphoric acid dibenzyl ester 4-(4-tert-butyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-ylmethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 10007240Phosphoric acid mono-[4-(4-tert-butyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-ylmethyl]ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve phosphoric acid dibenzyl ester 4-(4-tert-butyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-ylmethyl ester (225 mg, 0.316 mmol) in methanol and add 10% palladium on carbon (218 mg). Stir the solution for 2 hours under 1 atmosphere of hydrogen gas. Filter the solution through celite and wash through with additional methanol. Concentrate under reduced pressure and triturate with ether to yield the desired product as a yellow solid.

Workup

  1. filtrationFilter the solution through celite
  2. washwash through with additional methanol
  3. concentrationConcentrate under reduced pressure
  4. customtriturate with ether

Sources & evidence

ORD record
ord-5ff7288dc24447ca9f13e0f433722e70
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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