Formamidine acetate → 7-Benzyloxy-6-methoxy-3H-quinazolin-4-one

HRID 407272Notes

Reaction equation

[NH2:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([O:26][CH3:27])=[CH:14][C:3]=1[C:4](OCC1C=CC=CC=1)=[O:5].C(O)(=O)C.[CH:32](N)=[NH:33]>C(O)C(C)C>[CH2:19]([O:18][C:16]1[CH:17]=[C:2]2[C:3]([C:4](=[O:5])[NH:33][CH:32]=[N:1]2)=[CH:14][C:15]=1[O:26][CH3:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 97 °C

Procedure

Benzyl 2-amino-4-(benzyloxy)-5-methoxybenzoate (5.55 kg), formamidine acetate (2.2 kg) and isobutanol (33.3 L) were mixed. The reaction mixture was then heated to 97° C. and stirred at this temperature for 6 hours. The reaction mixture was then cooled to 25° C. over a period of at least an hour and then stirred at this temperature for 30 minutes. The product (7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one) was isolated by filtration, washed with isobutanol (6.1 L) and dried in the vacuum oven at a temperature of from 40 to 45° C.

Workup

temperatureThe reaction mixture was then cooled to 25° C. over a period of at least an hour
stirringstirred at this temperature for 30 minutes

Sources & evidence

ORD record: ord-d93a33bf37b94709a2484ea6cf8ead6d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754240B2

Reaction notes

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