L-Methionine → 4-Chloro-7-methoxyquinazolin-6-yl acetate

HRID 1666241Notes

Reaction equation

C[O:2][C:3]1[CH:4]=C2C(=CC=1OC)NC(=O)N=C2.CS(O)(=O)=O.N[C@H](C(O)=O)CCSC.[OH:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][C:40]=1[O:41][CH3:42])[NH:37][C:36](=O)[N:35]=[CH:34]2.O=S(Cl)[Cl:46]>>[Cl:46][C:34]1[C:33]2[C:38](=[CH:39][C:40]([O:41][CH3:42])=[C:31]([O:30][C:3](=[O:2])[CH3:4])[CH:32]=2)[N:37]=[CH:36][N:35]=1

Participants

Reactant 5

HCID 6137L-Methionine

HCID 6395Methanesulfonic Acid

HCID 24386Thionyl Chloride

HCID 127263032(1H)-Quinazolinone, 6,7-dimethoxy-

HCID 674343496-Hydroxy-7-methoxy-quinazolone

Product 1

HCID 220221604-Chloro-7-methoxyquinazolin-6-yl acetate

Procedure

6,7-dimethoxy-quinazolone was reacted with methanesulfonic acid and L-methionine under reflux for 2 h, and then the mixture was poured into ice water to deposit a solid, which is 6-hydroxy-7-methoxy-quinazolone intermediate. After the hydroxyl group therein was protected by acylation, the intermediate was treated with SOCl2 to obtain 4-chloro-6-acetoxy-7-methoxy-quinazoline.

Workup

temperatureunder reflux for 2 h

Sources & evidence

ORD record: ord-56a3e43f350043149026fb0f72e55506
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044063B2

Reaction notes

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