3-Pyridinecarboxaldehyde → 1-Isopropyl-6,7-methylenedioxy-4-(3-pyridyl)-3,4-dihydro-quinazolin-2(1H)-one

HRID 1884376Notes

Reaction equation

HRID 1884376 reaction equation
[CH:1]([N:4]([C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1)[C:5]([NH2:7])=[O:6])([CH3:3])[CH3:2].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1>>[CH:1]([N:4]1[C:8]2[C:13](=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[CH:23]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[NH:7][C:5]1=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 1005551-(1,3-Benzodioxol-5-yl)-1-isopropylurea

Product 1

HCID 235056501-Isopropyl-6,7-methylenedioxy-4-(3-pyridyl)-3,4-dihydro-quinazolin-2(1H)-oneYield 36%

Procedure

This compound was synthesized from N-isopropyl-N-[3,4-(methylenedioxy)-phenyl]urea (238 mg) and 3-pyridinecarboxaldehyde (100 μL) by the procedure described in example 10 in 36% yield, mp: 172-174° C. 1H NMR (CDCl3): 8.58-8.56 (m, 3H), 7.63 (m, 1H), 7.29 (m, 2H), 6.70 (s, 1H), 6.34 (s, 1H), 5.94 (d, J=1.3, 1H), 5.92 (d, J=1.3, 1H), 5.33 (s, 1H), 5.29 (s, 1H), 4.41 (m, 1H), 1.53 (d, J=6.8, 3H), 1.50 (d, J=6.8, 3H).

Sources & evidence

ORD record
ord-ea4eacbe11204486bfb707a8bbf2926e
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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