Ammonia → 6-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

HRID 2084028Notes

Reaction equation

HRID 2084028 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][O:20][CH2:19][CH2:18]1)[N:9]=[CH:8][N:7](COC(=O)C(C)(C)C)[C:6]2=[O:31].CO.N>C(Cl)Cl>[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][O:20][CH2:19][CH2:18]1)[N:9]=[CH:8][NH:7][C:6]2=[O:31]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 227322766-Methoxy-7-(3-morpholinopropoxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 1354371166-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-7-(3-morpholinopropoxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (1.85 g) was stirred in methylene chloride (20 ml) and methanol (20 ml) and methanolic ammonia (2M, 100 ml) was added. The reaction was stirred at ambient temperature for 48 hours, evaporated to dryness, and then stirred in diethyl ether for 1 hour. The reaction mixture was filtered affording 6-methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one as a solid, (1.22 g, 90%); NMR: 1.9 (m, 2H), 2.4 (broad m, 6H), 3.55 (m, 4H), 3.88 (s, 3H), 4.12 (m, 2H), 7.1 (s, 1H), 7.41 (s, 1H), 7.94 (s, 1H); m/s: M+H+ 320.

Workup

  1. customevaporated to dryness
  2. stirringstirred in diethyl ether for 1 hour
  3. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-d1ce9c2832854a91bd763fd852c8a3e6
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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