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

HRID 2113613Notes

Reaction equation

HRID 2113613 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]([C:24]3[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:8][CH:9]=2)[N:4]=1.[CH2:34]([O:41][P:42]([O-:52])([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11]2[C:10]3[C:5](=[CH:6][C:7]([C:24]4[C:29]([C:30]([F:32])([F:31])[F:33])=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:8][CH:9]=3)[N:4]=[C:3]([CH2:2][O:43][P:42](=[O:52])([O:44][CH2:45][C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[O:41][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:12]=2)=[CH:15][CH:16]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 4193600DibenzylphosphateHCID 58628208[2-Chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-t-butyl-phenyl)-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Heat a solution of [2-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-t-butyl-phenyl)-amine (417 mg, 0.89 mmol), Ag2O (308 mg, 1.33 mmol), and dibenzylphosphate (370 mg, 1.33 mmol) in acetonitrile at 70° C. for 18 hours. Dilute with additional acetonitrile and filter the hot solution through celite. Concentrate under reduced pressure to give a foam. Crystallize the crude product by dissolving in ether and slowly adding hexanes. Cool the resulting mixture on ice and collect the resulting solid via filtration to afford pure product.

Workup

  1. filtrationfilter the hot solution through celite
  2. concentrationConcentrate under reduced pressure
  3. customto give a foam
  4. customCrystallize the crude product
  5. dissolutionby dissolving in ether
  6. temperatureCool the resulting mixture on ice
  7. customcollect the resulting solid
  8. filtrationvia filtration
  9. customto afford pure product

Sources & evidence

ORD record
ord-593f3ae7d5fd4ab79e9f761f318487e0
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

Loading…