Ethyl orthoformate → HCID 12150183, compound

HRID 1993320Notes

Reaction equation

HRID 1993320 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]3[O:16][CH2:15][O:14][C:11]=3[CH:12]=2)[C:7]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([NH2:24])[CH:18]=2)=[N:6][C:5]1=[O:25])([CH3:3])[CH3:2].[CH:26](OCC)(OCC)OCC>CCOC(C)=O>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]3[O:16][CH2:15][O:14][C:11]=3[CH:12]=2)[CH:7]([C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH:26]=[N:24][C:19]=3[CH:18]=2)[NH:6][C:5]1=[O:25])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 135837650HCID 135837650, compound

Product 1

HCID 12150183HCID 12150183, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-isopropyl-6,7-methylenedioxy-4-(3-amino-4-hydroxyphenyl)quinazolin-2(1H)-one (93 mg) in triethyl orthoformate (3 mL) was refluxed for 1 h, cooled to rt, diluted with EtOAc (30 mL), washed with water, saturated aqueous solution of NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo to yield the title compound as a tan solid (70 mg, 71%), mp: 84-86° C. 1H NMR (CDCl3): 8.12 (s, 1H), 7.72 (s, 1H), 7.59 (d, J=8.3, 2H), 7.39 (d, J=8.3, 1H), 6.71 (s, 1H), 6.28 (s, 1H), 5.92 (s, 1H), 5.90 (s, 1H), 5.49 (s, 1H), 5.14 (s, 1H), 4.45 (m, 1H), 1.58 (d, J=6.6, 3H), 1.55 (d, J=6.6, 3H).

Workup

  1. washwashed with water, saturated aqueous solution of NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0adee12dfb51485b9887d333d0e4122f
Source dataset
uspto-grants-2010_01
Patent number
US07652006B2

Reaction notes

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