Water → 7-(2-(Piperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 1791749Notes

Reaction equation

HRID 1791749 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:26]=[C:25]3[C:20]([C:21](=[O:35])[N:22]([CH2:27][O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[CH:23]=[N:24]3)=[CH:19][C:18]=2[O:36][CH3:37])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:26]=[C:25]3[C:20]([C:21](=[O:35])[N:22]([CH2:27][O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:31])[CH3:32])[CH:23]=[N:24]3)=[CH:19][C:18]=2[O:36][CH3:37])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 110276937-(2-(1-Tert-butoxycarbonylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 117324937-(2-(Piperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-(2-(1-tert-butoxycarbonylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (10.5 g, 20 mmol) in methylene chloride (100 ml) containing TFA (25 ml) was stirred for 1 hour at ambient temperature. Water (50 ml) and methylene chloride (100 ml) were added and the pH of the aqueous layer was adjusted to 8 with solid sodium hydrogen carbonate. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was triturated with ether and the solid was filtered and dried under vacuum to give 7-(2-(piperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (8.3 g, 100%).

Workup

  1. customThe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated with ether
  6. filtrationthe solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b62228dabf2c4e3f8837fd4882fb76a8
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

Loading…