6-Methoxy-7-(3-piperidinopropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one → 6-Methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-one

HRID 454066Notes

Reaction equation

HRID 454066 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[N:9]=[CH:8][N:7](COC(=O)C(C)(C)C)[C:6]2=[O:31]>N.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[N:9]=[CH:8][NH:7][C:6]2=[O:31]

Participants

4

Reactant 1

HCID 218748076-Methoxy-7-(3-piperidinopropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 1354715536-Methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-oneYield 95.4%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of 6-methoxy-7-(3-piperidinopropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.35 g, 5.45 mmol) in 7M ammonia in methanol (50 ml) was stirred overnight at ambient temperature. The volatiles were removed under vacuum and the residue was triturated with ether, filtered and washed with ether followed by ether/methylene chloride (1/1) and dried under vacuum to give 6-methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-one (1.65 g, 95%).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue was triturated with ether
  3. filtrationfiltered
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b0442d53d5054018a05c4a5f64610a90
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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