Ethyl orthoformate → HCID 12150183, compound

HRID 991525Notes

Reaction equation

HRID 991525 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-21ff3f0dd6954700ae66635df02dd430
Source dataset
uspto-grants-2002_10
Patent number
US06465472B1

Reaction notes

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